Herbicidal benzoylisothiazoles

ABSTRACT

PCT No. PCT/EP97/01854 Sec. 371 Date Oct. 15, 1998 Sec. 102(e) Date Oct. 15, 1998 PCT Filed Apr. 14, 1997 PCT Pub. No. WO97/38987 PCT Pub. Date Oct. 23, 19974-Benzoylisothiazoles of the formula 1 wherein x is oxygen or sulfur; R1 is hydrogen, alkyl, alkenyl, alkynyl; or is optionally substituted alkoxycarbonyl, aryl, heterocyclyl or hetaryl; R2 is hydrogen, halogen, cyano, nitro, alkylsulfonyl or alkoxycarbonyl; or is optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, aryloxy, arylthio, alkylamino, arylamino, hetaryl or heterocyclyl; R3 is optionally substituted alkyl, cycloalkyl or aryl, or their salts, their manufacture and herbicidal compositions containing them.

This application is a 371 of PCT/EP97/01854 filed Apr. 14, 1997.

DESCRIPTION

The present invention relates to novel substituted benzoylisothiazoles,processes for their preparation, and their use as herbicides.

The patent literature (EP 0 527 036, EP 0 527 037, EP 0 560 482, EP 0580 439, EP 0 588 357, EP 609 797, EP 0 609 798, EP 0 636 622, WO94/14782, WO 94/18179, WO 95/15691 and WO 95/16678) disclosessubstituted 4-benzoyl-5-cycloalkylisoxazoles as a class of compoundswhich have a pronounced herbicidal activity pre-emergence.4-(2-Sulfonylmethyl-4-trifluoromethylbenzoyl)-5-cyclopropyl-isoxazole, arepresentative of this class of compound, is developed by Rhone-Poulencas a herbicidally active substance used pre-emergence against harmfulmono- and dicotyledons in maize (RPA 201772, Technical Bulletin).

Moreover, the herbicidal and insecticidal activity of substituted4-alkyl- and 4-cycloalkyl-5-aryl- or -5-hetarylisoxazoles has beendisclosed (GB 2 284 600, WO 95/ 22903, WO 95/22904 and WO 95/25105).

The herbicidal activity of the known compounds is not onlyinsufficiently effective post-emergence, but also only partlysatisfactory pre-emergence and combined with incomplete crop plantcompatibility.

Herbicidal or insecticidal 4-benzoylisothiazoles according to theinvention have not been found in the prior art as yet.

As yet, 4-benzoylisothiazoles have only been of moderate interest with aview to their synthesis. While substituted isothiazoles and theircarbocycle-fused derivatives have been the object of basicinvestigations (for example: D. L. Pain, B. J. Peart, K. R. H.Wooldridge, Comprehensive Heterocyclic Chemistry, Vol. 6, Part 4B, p.131, Ed. A. R. Katritzky, Pergamon Press, Oxford 1984), only individualcases of acylated and, in particular, benzoylated derivatives have beendescribed in the literature (for example: A. J. Layton, E. Lunt, J.Chem. Soc. (1968) 611, A. Alberola, F. Alonso, P. Cuadrado, C. M.Sanudo, Synth. Commun. 17 (1987) 1207, A. Alberola, F. Alonso, P.Cuadrado, C. M. Sanudo, J. Heterocycl. Chem. 25 (1988) 235).

Some hydroxypropylaminocarbonyl-substituted 4-benzoylisothiazoles havebeen investigated in EP 0 524 781 and EP 0 617 010 as muscle-relaxingagents and as suitable therapeutic amides to treat incontinence. EP 0449 223 maintains that3,5-di(tertiary-butyl)-4-hydroxybenzoylisothiazoles are inhibitors of5-lipoxygenase and cyclooxygenase and thus have an antiinflammatoryaction.

It is an object of the present invention to provide novel herbicidallyactive ingredients with an improved profile of action and improved cropplant compatibility.

Surprisingly, the benzoylisothiazoles of the general formula 1 accordingto the invention show a pronounced herbicidal activity against harmfulplants combined with crop plant compatibility.

The present invention relates to 4-benzoylisothiazoles of the generalformula 1 ##STR2## where the substituents have the following meanings: Xis oxygen or sulfur;

R¹ is hydrogen, alkyl, alkenyl, alkynyl; unsubstituted or substitutedalkoxycarbonyl; unsubstituted or substituted aryl, unsubstituted orsubstituted heterocyclyl or unsubstituted or substituted hetaryl;

R² is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, itbeing possible for these radicals to have attached to them one or moreof the following groups: halogen, alkyl, alkenyl or alkynyl; aryl, itbeing possible for this radical to have attached to it one or more ofthe following groups: alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy,alkynyloxy, alkylthio or alkenylthio, it being possible for theseradicals to be partially or fully halogenated or to have attached tothem one or more of the following groups:

alkoxy, alkenyloxy, aryloxy, alkylsulfonyl, alkenylsulfonyl orarylsulfonyl;

alkylsulfonyl or alkoxycarbonyl;

unsubstituted or substituted aryloxy or unsubstituted or substitutedarylthio;

unsubstituted or substituted mono- or dialkylamino, unsubstituted orsubstituted mono- or diarylamino or unsubstituted or substitutedN-alkyl-N-arylamino, it being possible for alkyl and aryl to beidentical or different;

halogen, cyano or nitro;

hetaryl or heterocyclyl, it being possible for these radicals to bepartially or fully halogenated or to have attached to them one or moreof the following groups:

alkyl, alkoxy or aryl, it being possible in the case of heterocyclyl forat least one of the nitrogens to have attached to it one of thefollowing groups:

alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, alkoxy, alkenyloxy,alkynyloxy, cycloalkyloxy, haloalkoxy, unsubstituted or substituted arylor unsubstituted or substituted aryloxy;

R³ is alkyl or cycloalkyl, it being possible for these radicals to bepartially or fully halogenated or to have attached to them one or moreof the following groups:

alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio,alkenylthio, alkynylthio, alkoxycarbonyl, alkenyloxycarbonyl,alkynyloxycarbonyl, haloalkyl, haloalkenyl, haloalkynyl, haloalkoxy,haloalkenyloxy, haloalkynyloxy, haloalkylthio, haloalkenylthio,haloalkynylthio, haloalkoxycarbonyl, haloalkenyloxycarbonyl orhaloalkynyloxycarbonyl;

a radical of the general formula 2 ##STR3## where the substituents havethe following meanings: R⁴ -R⁸ can be identical or different andindependently of one another are hydrogen, alkyl, alkenyl, alkynyl,cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl,cycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, hydroxyl,alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkylalkoxy,cycloalkylalkenyloxy, cycloalkylalkynyloxy, cycloalkenyloxy, aryloxy,arylalkoxy, arylalkenyloxy, arylalkynyloxy, thio, alkylthio,alkenylthio, alkynylthio, cycloalkylthio, cycloalkylalkylthio,cycloalkylalkenylthio, cycloalkylalkynylthio, cycloalkenylthio,arylthio, arylalkylthio, arylalkenylthio, arylalkynylthio, amino,unsubstituted or substituted mono- or dialkylamino, unsubstituted orsubstituted mono- or diarylamino, unsubstituted or substitutedN-alkyl-N-arylamino, it being possible for alkyl and aryl to beidentical or different, alkenylamino, alkynylamino, cycloalkylamino,cycloalkenylamino, sulfonyl, alkylsulfonyl, alkenylsulfonyl,alkynylsulfonyl, cycloalkylsulfonyl, cycloalkylalkylsulfonyl,cycloalkylalkenylsulfonyl, cycloalkylalkynylsulfonyl, arylsulfonyl,arylalkylsulfonyl, arylalkenylsulfonyl, arylalkynylsulfonyl, sulfoxyl,alkylsulfoxyl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl,cycloalkylalkylsulfoxyl, cycloalkylalkenylsulfoxyl,cycloalkylalkynylsulfoxyl, arylsulfoxyl, arylalkylsulfoxyl,arylalkenylsulfoxyl, arylalkynylsulfoxyl, unsubstituted or substitutedmono- or dialkylaminosulfonyl, unsubstituted or substituted mono- ordiarylaminosulfonyl, unsubstituted or substitutedN-alkyl-N-arylaminosulfonyl, it being possible for alkyl and aryl to beidentical or different, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl,cycloalkylcarbonyl, cycloalkylalkylcarbonyl, cycloalkylalkenylcarbonyl,cycloalkylalkynylcarbonyl, arylcarbonyl, arylalkylcarbonyl,arylalkenylcarbonyl, arylalkynylcarbonyl, carboxyl, alkoxycarbonyl,alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl,cycloalkylalkoxycarbonyl, cycloalkylalkenyloxycarbonyl,cycloalkylalkynyloxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl,arylalkenyloxycarbonyl, arylalkynyloxycarbonyl, aminocarbonyl,unsubstituted or substituted mono- or dialkylaminocarbonyl,unsubstituted or substituted mono- or diarylaminocarbonyl, unsubstitutedor substituted N-alkyl-N-arylaminocarbonyl, it being possible for alkyland aryl to be identical or different, unsubstituted or substitutedmono- or dialkylcarbonylamino, unsubstituted or substituted mono- ordiarylcarbonylamino, unsubstituted or substitutedN-alkyl-N-arylcarbonylamino, it being possible for alkyl and aryl to beidentical or different, alkoxyaminocarbonyl, alkenyloxycarbonylamino,alkynyloxycarbonylamino, cycloalkoxycarbonylamino,cycloalkylalkoxycarbonylamino, cycloalkylalkenyloxycarbonylamino,cycloalkylalkynyloxycarbonylamino, aryloxycarbonylamino,arylalkoxycarbonylamino, arylalkenyloxycarbonylamino,arylalkynyloxycarbonylamino, halogen, haloalkyl, haloalkenyl,haloalkynyl, haloalkoxy, haloalkenyloxy, haloalkynyloxy haloalkylthio,haloalkenylthio, haloalkynylthio, haloalkylamino, haloalkenylamino,haloalkynylamino, haloalkylsulfonyl, haloalkenylsulfonyl,haloalkynylsulfonyl, haloalkylsulfoxyl, haloalkenylsulfoxyl,haloalkynylsulfoxyl, haloalkylcarbonyl, haloalkenylcarbonyl,haloalkynylcarbonyl, haloalkoxycarbonyl, haloalkenyloxycarbonyl,haloalkynyloxycarbonyl, haloalkylaminocarbonyl,haloalkenylaminocarbonyl, haloalkynylaminocarbonyl,haloalkoxycarbonylamino, haloalkenyloxycarbonylamino,haloalkynyloxycarbonylamino; cyano or nitro or one of the followinggroups: ##STR4## with the exception of4-(4'-chlorobenzoyl)-3-methylisothiazole,4-benzoyl-3,5-dimethylisothiazole,4-(4'-hydroxymethylcarbonylaminobenzoyl)isothiazole and4-(3',5'-di-tertiary-butyl-4'-hydroxybenzoyl)isothiazole;

R⁴, R⁵ together can form a five- or six-membered, saturated orunsaturated, aromatic or non-aromatic, unsubstituted or substitutedalkylene, alkenylene or alkdienylene chain;

R⁵, R⁶ together can form a five- or six-membered, saturated orunsaturated, aromatic or non-aromatic, unsubstituted or substitutedalkylene, alkenylene or alkdienylene chain;

and to salts of the 4-benzoylisothiazoles of the general formula 1 whichare conventionally used in agriculture.

In the definitions of the compounds I given at the outset, collectiveterms were used which generally represent the following groups:

halogen: fluorine, chlorine, bromine and iodine;

alkyl: straight-chain or branched alkyl groups having 1 to 6 or 10carbon atoms, for example C₁ -C₆ -alkyl such as methyl, ethyl, propyl,1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl,1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl,1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl,4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;

alkylamino: an amino group which has attached to it a straight-chain orbranched alkyl group having 1 to 6 carbon atoms as mentioned above;

dialkylamino: an amino group which has attached to it two mutuallyindependent straight-chain or branched alkyl groups having in each case1 to 6 carbon atoms as mentioned above;

alkylcarbonyl: straight-chain or branched alkyl groups having 1 to 10carbon atoms which are bonded to the skeleton via a carbonyl group(--CO--);

alkylsulfonyl: straight-chain or branched alkyl groups having 1 to 6 or10 carbon atoms which are bonded to the skeleton via a sulfonyl group(--SO₂ --);

alkylsulfoxyl: straight-chain or branched alkyl groups having 1 to 6carbon atoms which are bonded to the skeleton via a sulfoxyl group(--S(═O)--);

alkylaminocarbonyl: alkylamino groups having 1 to 6 carbon atoms asmentioned above which are bonded to the skeleton via a carbonyl group(--CO--);

dialkylaminocarbonyl: dialkylamino groups having in each case 1 to 6carbon atoms per alkyl radical as mentioned above which are bonded tothe skeleton via a carbonyl group (--CO--);

alkylaminothiocarbonyl: alkylamino groups having 1 to 6 carbon atoms asmentioned above which are bonded to the skeleton via a thiocarbonylgroup (--CS--);

dialkylaminothiocarbonyl: dialkylamino groups having in each case 1 to 6carbon atoms per alkyl radical as mentioned above which are bonded tothe skeleton via a thiocarbonyl group (--CS--);

haloalkyl: straight-chain or branched alkyl groups having 1 to 6 carbonatoms, it being possible for some or all of the hydrogen atoms in thesegroups to be replaced by halogen atoms as mentioned above, eg. C₁ -C₂-haloalkyl, such as chloromethyl, dichloromethyl, trichloromethyl,fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl,dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;

alkoxy: straight-chain or branched alkyl groups having 1 to 6 carbonatoms as mentioned above which are bonded to the skeleton via an oxygenatom (--O--), eg. C₁ -C₆ -alkoxy, such as methyloxy, ethyloxy,propyloxy, 1-methylethyloxy, butyloxy, 1-methyl-propyloxy,2-methylpropyloxy, 1,1-dimethylethyloxy, pentyloxy, 1-methylbutyloxy,2-methylbutyloxy, 3-methylbutyloxy, 2,2-dimethylpropyloxy,1-ethylpropyloxy, hexyloxy, 1,1-dimethylpropyloxy,1,2-dimethylpropyloxy, 1-methylpentyloxy, 2-methylpentyloxy,3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutyloxy,1,2-dimethylbutyloxy, 1,3-dimethylbutyloxy, 2,2-dimethylbutyloxy,2,3-dimethylbutyloxy, 3,3-dimethylbutyloxy, 1-ethylbutyloxy,2-ethylbutyloxy, 1,1,2-trimethylpropyloxy, 1,2,2-trimethylpropyloxy,1-ethyl-1-methylpropyloxy and 1-ethyl-2-methylpropyloxy;

alkoxycarbonyl: straight-chain or branched alkyl groups having 1 to 6carbon atoms which are bonded to the skeleton via an oxycarbonyl group(--OC(═O)--);

haloalkoxy: straight-chain or branched alkyl groups having 1 to 6 carbonatoms, it being possible for some or all of the hydrogen atoms in thesegroups to be replaced by halogen atoms as mentioned above, and thesegroups being bonded to the skeleton via an oxygen atom;

alkylthio: straight-chain or branched alkyl groups having 1 to 4 or 6carbon atoms as mentioned above which are bonded to the skeleton via asulfur atom (--S--), eg. C₁ -C₆ -alkylthio, such as methylthio,ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio,2-methylpropylthio, 1,1-dimethylethylthio, pentylthio,1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio,2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio,1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio,2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio,1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio,2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio,1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio,1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and1-ethyl-2-methylpropylthio;

cycloalkyl: monocyclic alkyl groups having 3 to 6 carbon ring members,eg. cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

alkenyl: straight-chain or branched alkenyl groups having 2 to 6 or 10carbon atoms and a double bond in any position, eg. C₂ -C₆ -alkenyl,such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl,2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl,1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl,3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl,3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl,3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl,3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

akenyloxy: straight-chain or branched alkenyl groups having 2 to 6carbon atoms and a double bond in any position which are bonded to theskeleton via an oxygen atom (--O--);

alkenylthio and alkenylamino: straight-chain or branched alkenyl groupshaving 2 to 6 carbon atoms and a double bond in any position which arebonded to the skeleton via a sulfur atom (alkenylthio) or via a nitrogenatom (alkenylamino).

alkenylcarbonyl: straight-chain or branched alkenyl groups having 2 to10 carbon atoms and a double bond in any position which are bonded tothe skeleton via a carbonyl group (--CO--);

alkynyl: straight-chain or branched alkynyl groups having 2 to 10 carbonatoms and a triple bond in any position, eg. C₂ -C₆ -alkynyl, such asethynyl, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl,2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl,1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl,1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl,1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl,2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl,4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl,1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl,1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;

alkynyloxy, alkynylthio and alkynylamino: straight-chain or branchedalkynyl groups having 2 to 6 carbon atoms and a triple bond in anyposition which are bonded to the skeleton via an oxygen atom(alkynyloxy), via a sulfur atom (alkynylthio) or via a nitrogen atom(alkynylamino).

Alkynylcarbonyl: straight-chain or branched alkynyl groups having 3 to10 carbon atoms and a triple bond in any position which are bonded tothe skeleton via a carbonyl group (--CO--);

cycloalkenyl; cycloalkenyloxy, cycloalkenylthio and cycloalkenylamino:monocyclic alkenyl groups having 3 to 6 carbon ring members which arebonded to the skeleton directly; or via an oxygen atom (cycloalkenyloxy)or via a sulfur atom (cycloalkenylthio) or via a nitrogen atom(cycloalkenylamino), eg. cyclopropenyl, cyclobutenyl, cyclopentenyl orcyclohexenyl;

cycloalkoxy, cycloalkylthio and cycloalkylamino: monocyclic alkyl groupshaving 3 to 6 carbon ring members which are bonded to the skeleton viaan oxygen atom (cycloalkyloxy), via a sulfur atom (cycloalkylthio) orvia a nitrogen atom (cycloalkylamino), eg. cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl;

cycloalkylcarbonyl: cycloalkyl groups as defined above which are bondedto the skeleton via a carbonyl group (--CO--);

cycloalkoxycarbonyl: cycloalkoxy groups as defined above which arebonded to the skeleton via a carbonyl group (--CO--);

alkenyloxycarbonyl: alkenyloxy groups as defined above which are bondedto the skeleton via a carbonyl group (--CO--);

alkynyloxycarbonyl: alkynyloxy groups as defined above which are bondedto the skeleton via a carbonyl group (--CO--);

heterocyclyl: three- to six-membered saturated or partially unsaturatedmono- or polycyclic heterocycles which contain one to three hetero atomsselected from a group consisting of oxygen, nitrogen and sulfur andwhich are bonded to the skeleton directly via carbon, eg.2-tetrahydrofuranyl, oxiranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl,3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl,4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl,4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl,4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl,5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl,2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl,1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl,1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl,1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl,1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl,2,3-dihydro-fur-4-yl, 2,3-dihydro-fur-5-yl, 2,5-dihydro-fur-2-yl,2,5-dihydro-fur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl,2,3-dihydrothien-4-yl, 2,3-dihydrothien-5-yl, 2,5-dihydrothien-2-yl,2,5-dihydrothien-3-yl, 2,3-dihydropyrrol-2-yl, 2,3-dihydropyrrol-3-yl,2,3-dihydropyrrol-4-yl, 2,3-dihydropyrrol-5-yl, 2,5-dihydropyrrol-2-yl,2,5-dihydropyrrol-3-yl, 2,3-dihydroisoxazol-3-yl,2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl,4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl,4,5-dihydroisoxazol-5-yl, 2,5-dihydroisothiazol-3-yl,2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl,2,3-dihydroisopyrazol-3-yl, 2,3-dihydroisopyrazol-4-yl,2,3-dihydroisopyrazol-5-yl, 4,5-dihydroisopyrazol-3-yl,4,5-dihydroisopyrazol-4-yl, 4,5-dihydroisopyrazol-5-yl,2,5-dihydroisopyrazol-3-yl, 2,5-dihydroisopyrazol-4-yl,2,5-dihydroisopyrazol-5-yl, 2,3-dihydrooxazol-3-yl,2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrooxazol-3-yl,4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-3-yl,2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl, 2,3-dihydrothiazol-2-yl,2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl,4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl,4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl,2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl,2,3-dihydroimidazol-2-yl, 2,3-dihydroimidazol-4-yl,2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl,4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl,2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl,2,5-dihydroimidazol-5-yl, 2-morpholinyl, 3-morpholinyl, 2-piperidinyl,3-piperidinyl, 4-piperidinyl, 3-tetrahydropyridazinyl,4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl,4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl,1,3,5-tetrahydrotriazin-2-yl, 1,2,4-tetrahydrotriazin-3-yl,1,3-dihydrooxazin-2-yl, 1,3-dithian-2-yl, 2-tetrahydropyranyl,1,3-dioxolan-2-yl, 3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3-thiazin-2-yl,4H-3,1-benzothiazin-2-yl, 1,1-dioxo-2,3,4,5-tetrahydrothien-2-yl,2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl,1,3-dihydrooxazin-2-yl, 1,3-dithian-2-yl,

aryl: aryloxy, arylthio, arylcarbonyl, aryloxycarbonyl, arylsulfonyl andarylsulfoxyl: aromatic mono- or polycyclic hydrocarbon radicals whichare bonded to the skeleton directly; or (aryloxy) via an oxygen atom(--O--), or (arylthio) via a sulfur atom (--S--), or (arylcarbonyl) viaa carbonyl group (--CO--), or (aryloxycarbonyl) via an oxycarbonyl group(--OCO--), or (arylsulfonyl) via a sulfonyl group (--SO₂ --) or(arylsulfoxyl) via a sulfoxyl group (--SO--), eg. phenyl, naphthyl andphenanthrenyl; phenyloxy, naphthyloxy and phenanthrenyloxy and thecorresponding carbonyl and sulfonyl radicals;

arylamino: aromatic mono- or polycyclic hydrocarbon radicals which arebonded to the skeleton via a nitrogen atom.

Hetaryl: aromatic mono- or polycyclic radicals which, besides carbonring members, additionally contain one to four nitrogen atoms or one tothree nitrogen atoms and an oxygen or a sulfur atom or an oxygen or asulfur atom and which are bonded to the skeleton directly via carbon,eg.

5-membered hetaryl containing one to three nitrogen atoms: 5-memberedhetaryl ring groups which, besides carbon atoms, can contain one tothree nitrogen atoms as ring members, eg. 2-pyrrolyl, 3-pyrrolyl,3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl,1,2,4-triazol-3-yl and 1,3,4-triazol-2-yl;

5-membered hetaryl containing one to four nitrogen atoms or one to threenitrogen atoms and a sulfur or oxygen atom or an oxygen or a sulfuratom: 5-membered hetaryl ring groups which, besides carbon atoms, cancontain one to four nitrogen atoms or one to three nitrogen atoms and asulfur or oxygen atom or an oxygen or sulfur atom as ring members, eg.2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl,3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl,4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl,2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl,5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl,1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl,1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl,1,3,4-triazol-2-yl;

carbocycle-fused 5-membered hetaryl containing one to three nitrogenatoms or a nitrogen atom and/or an oxygen or sulfur atom: 5-memberedhetaryl ring groups which, besides carbon atoms, can contain one to fournitrogen atoms or one to three nitrogen atoms and a sulfur or oxygenatom or an oxygen or a sulfur atom as ring members and in which twoadjacent carbon ring members or a nitrogen and an adjacent carbon ringmember can be bridged by a buta-1,3-diene-1,4-diyl group;

6-membered hetaryl containing one to three, or one to four. nitrogenatoms: 6-membered hetaryl ring groups which, besides carbon atoms, cancontain one to three, or one to four, nitrogen atoms as ring members,eg. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl,2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl,1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-tetrazin-3-yl;

benzo-fused 6-membered hetaryl containing one to four nitrogen atoms:6-membered hetaryl ring groups in which two adjacent carbon ring memberscan be bridged by a buta-1,3-diene-1,4-diyl group, eg. quinoline,isoquinoline, quinazoline and quinoxaline,

and the corresponding oxy, thio, carbonyl or sulfonyl groups.

The term "partially or fully halogenated" expresses that in groups thuscharacterized some or all of the hydrogen atoms can be replaced byidentical or different halogen atoms as mentioned above.

Unsubstituted or substituted means that the organic group in questioncan be substituted as desired, all substituents listed in the presentapplication being suitable in principle.

Preferred substituents are hydrogen, alkyl, alkenyl, alkynyl, preferablycycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, aryl, arylalkyl,arylalkenyl, hydroxyl, alkoxy, alkenyloxy, cycloalkoxy,cycloalkylalkoxy, aryloxy, arylalkoxy, thio, alkylthio, alkenylthio,cycloalkylthio, cycloalkylalkylthio, arylthio, arylalkylthio, amino,unsubstituted or substituted mono- or dialkylamino, unsubstituted orsubstituted mono- or diarylamino, unsubstituted or substitutedN-alkyl-N-arylamino, it being possible for alkyl and aryl to beidentical or different, alkenylamino, cycloalkylamino,cycloalkenylamino, sulfonyl, alkylsulfonyl, alkenylsulfonyl,cycloalkylsulfonyl, cycloalkylalkylsulfonyl, arylsulfonyl,arylalkylsulfonyl, sulfoxyl, alkylsulfoxyl, alkenylsulfoxyl,cycloalkylsulfoxyl, cycloalkylalkylsulfoxyl, arylsulfoxyl,arylalkylsulfoxyl, alkylcarbonyl, alkenylcarbonyl, cycloalkylcarbonyl,cycloalkylalkylcarbonyl, arylcarbonyl, arylalkylcarbonyl, carboxyl,alkoxycarbonyl, alkenyloxycarbonyl, cycloalkoxycarbonyl,cycloalkylalkoxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl,aminocarbonyl, unsubstituted or substituted mono- ordialkylaminocarbonyl, unsubstituted or substituted mono- ordiarylaminocarbonyl, unsubstituted or substitutedN-alkyl-N-arylaminocarbonyl, it being possible for alkyl and aryl to beidentical or different, alkoxyaminocarbonyl, alkenyloxycarbonylamino,cycloalkoxycarbonylamino, aryloxycarbonylamino, arylalkoxycarbonylamino,halogen, haloalkyl, haloalkenyl, unsubstituted or substituted mono- ordialkylamino, haloalkoxy, haloalkenyloxy, haloalkylthio,haloalkenylthio, haloalkylamino, haloalkenylamino, haloalkylsulfonyl,haloalkenylsulfonyl, haloalkylsulfoxyl, haloalkenylsulfoxyl,haloalkylcarbonyl, haloalkenylcarbonyl, haloalkoxycarbonyl,haloalkenyloxycarbonyl, haloalkylaminocarbonyl,haloalkenylaminocarbonyl, haloalkoxycarbonylamino,haloalkenyloxycarbonylamino, cyano or nitro.

Especially preferred substituents are hydrogen, alkyl, alkenyl,cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, hydroxyl, alkoxy,cycloalkoxy, aryloxy, thio, alkylthio, cycloalkylthio, arylthio, amino,unsubstituted or substituted mono- or dialkylamino, unsubstituted orsubstituted mono- or diarylamino, unsubstituted or substitutedN-alkyl-N-arylamino, it being possible for alkyl and aryl to beidentical or different, cycloalkylamino, sulfonyl, alkylsulfonyl,cycloalkylsulfonyl, arylsulfonyl, sulfoxyl, alkylsulfoxyl, arylsulfoxyl,alkylcarbonyl, arylcarbonyl, carboxyl, alkoxycarbonyl, aryloxycarbonyl,aminocarbonyl, unsubstituted or substituted mono- ordialkylaminocarbonyl, unsubstituted or substituted mono- ordiarylaminocarbonyl, unsubstituted or substitutedN-alkyl-N-arylaminocarbonyl, it being possible for alkyl and aryl to beidentical or different, alkoxyaminocarbonyl, aryloxycarbonylamino,halogen, haloalkyl, haloalkoxy, haloalkylthio, haloalkylamino,haloalkylsulfonyl, haloalkylsulfoxyl, haloalkylcarbonyl,haloalkoxycarbonyl, haloalkoxycarbonylamino, cyano or nitro.

Preferred compounds of the general formula 1 with a view to theirbiological activity are those where X is oxygen.

Furthermore, preferred compounds of the general formula 1 are thosewhere R¹ is hydrogen or unsubstituted or substituted alkoxycarbonyl.

Also preferred compounds of the general formula 1 are those where R¹ ishydrogen or alkoxycarbonyl having 1 to 6 carbon atoms which can be mono-or polysubstituted by fluorine, chlorine or bromine.

Especially preferred compounds of the formula 1 are those where R¹ ishydrogen, methoxycarbonyl or ethoxycarbonyl.

Furthermore, preferred compounds of the general formula 1 are thosewhere R² is alkyl having 1 to 6 carbon atoms, especially preferablymethyl, ethyl, isopropyl or tertiary butyl; or cycloalkyl having 3 to 6carbon atoms, especially preferably cyclopropyl or 1-methylcyclopropyl;or aryl, it being possible for this radical to have attached to it oneor more of the following groups:

alkyl, alkoxy, alkylthio, it being possible for these radicals to bepartially or fully halogenated, or halogen, especially preferably3-trifluoromethylaryl, 2,4-difluoroaryl; hetaryl or heterocyclyl, itbeing possible for these radicals to be partially or fully halogenatedor to have attached to them one or more of the following groups: alkyl,alkoxy or aryl, especially preferably 1,3-benzodioxol,2,2-difluoro-1,3-benzodioxol, 1,3-benzoxathiol,3,3-dioxo-1,3-benzoxathiol, benzoxazole, pyrazolyl or thienyl.

Furthermore, preferred compounds of the general formula 1 are thosewhere R³ is a radical of the general formula 2 ##STR5## where thesubstituents have the following meanings: R⁴ -R⁸ can be identical ordifferent and independently of one another are hydrogen, alkyl,cycloalkyl, aryl, hydroxyl, alkoxy, cycloalkoxy, aryloxy, thio,alkylthio, cycloalkylthio, arylthio, amino, in each case unsubstitutedor substituted mono- or dialkylamino or mono- or diarylamino orN-alkyl-N-arylamino, it being possible for alkyl and aryl to beidentical or different, cycloalkylamino, sulfonyl, alkylsulfonyl,cycloalkylsulfonyl, arylsulfonyl, sulfoxyl, alkylsulfoxyl,cycloalkylsulfoxyl, arylsulfoxyl, alkylcarbonyl, cycloalkylcarbonyl,arylcarbonyl, carboxyl, alkoxycarbonyl, cycloalkoxycarbonyl,aryloxycarbonyl, aminocarbonyl, in each case unsubstituted orsubstituted mono- or dialkylaminocarbonyl or mono- ordiarylaminocarbonyl or N-alkyl-N-arylaminocarbonyl, it being possiblefor alkyl and aryl to be identical or different, alkoxyaminocarbonyl,cycloalkoxycarbonylamino, aryloxycarbonylamino, halogen, haloalkyl,haloalkoxy, haloalkylthio, haloalkylamino, haloalkylsulfonyl,haloalkylsulfoxyl, haloalkylcarbonyl, haloalkoxycarbonyl,haloalkylaminocarbonyl, haloalkoxycarbonylamino; cyano or nitro;

R⁴, R⁵ together can form a five- or six-membered, saturated orunsaturated, aromatic or non-aromatic, unsubstituted or substitutedalkylene, alkenylene or alkdienylene chain;

R⁵, R⁶ together can form a five- or six-membered, saturated orunsaturated, aromatic or non-aromatic, unsubstituted or substitutedalkylene, alkenylene or alkdienylene chain.

Other preferred compounds of the general formula 1 are those where R³ isa radical of the general formula 2a-g ##STR6## where the substituentshave the following meanings: R⁴ -R⁸ can be identical or different andindependently of one another are alkyl, alkenyl, alkynyl, cycloalkyl,cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, aryl, arylalkyl,arylalkenyl, arylalkynyl, hydroxyl, alkoxy, alkenyloxy, alkynyloxy,cycloalkoxy, cycloalkylalkoxy, cycloalkylalkenyloxy,cycloalkylalkynyloxy, aryloxy, arylalkoxy, arylalkenyloxy,arylalkynyloxy, thio, alkylthio, alkenylthio, alkynylthio,cycloalkylthio, cycloalkylalkylthio, cycloalkylalkenylthio,cycloalkylalkynylthio, arylthio, arylalkylthio, arylalkenylthio,arylalkynylthio, amino, unsubstituted or substituted mono- ordialkylamino, unsubstituted or substituted mono- or diarylamino,unsubstituted or substituted N-alkyl-N-arylamino, it being possible foralkyl and aryl to be identical or different, sulfonyl, alkylsulfonyl,cycloalkylsulfonyl, cycloalkylalkylsulfonyl, cycloalkylalkenylsulfonyl,cycloalkylalkynylsulfonyl, arylsulfonyl, arylalkylsulfonyl,arylalkenylsulfonyl, arylalkynylsulfonyl, sulfoxyl, alkylsulfoxyl,alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl,cycloalkylalkylsulfoxyl, cycloalkylalkenylsulfoxyl,cycloalkylalkynylsulfoxyl, arylsulfoxyl, arylalkylsulfoxyl,arylalkenylsulfoxyl, arylalkynylsulfoxyl, aminosulfonyl, unsubstitutedor substituted mono- or dialkylaminosulfonyl, unsubstituted orsubstituted mono- or diarylaminosulfonyl, unsubstituted or substitutedN-alkyl-N-arylaminosulfonyl, it being possible for alkyl and aryl to beidentical or different, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl,cycloalkylcarbonyl, cycloalkylalkylcarbonyl, cycloalkylalkenylcarbonyl,cycloalkylalkynylcarbonyl, arylcarbonyl, arylalkylcarbonyl,arylalkenylcarbonyl, arylalkynylcarbonyl, carboxyl, alkoxycarbonyl,alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl,cycloalkylalkoxycarbonyl, cycloalkylalkenyloxycarbonyl,cycloalkylalkynyloxycarbonyl, arylcarbonyl, arylalkoxycarbonyl,arylalkenyloxycarbonyl, arylalkynyloxycarbonyl, aminocarbonyl,unsubstituted or substituted mono- or dialkylaminocarbonyl,unsubstituted or substituted mono- or diarylaminocarbonyl, unsubstitutedor substituted N-alkyl-N-arylaminocarbonyl, it being possible for alkyland aryl to be identical or different, unsubstituted or substitutedmono- or dialkylcarbonylamino, unsubstituted or substituted mono- ordiarylcarbonylamino, unsubstituted or substitutedN-alkyl-N-arylcarbonylamino, it being possible for alkyl and aryl to beidentical or different, alkoxyaminocarbonyl, alkenyloxycarbonylamino,alkynyloxycarbonylamino, cycloalkoxycarbonylamino,cycloalkylalkoxycarbonylamino, cycloalkylalkenyloxycarbonylamino,cycloalkylalkynyloxycarbonylamino, aryloxycarbonylamino,arylalkoxycarbonylamino, arylalkenyloxycarbonylamino,arylalkynyloxycarbonylamino, halogen, haloalkyl, haloalkenyl,haloalkynyl, haloalkoxy, haloalkenyloxy, haloalkynyloxy, haloalkylthio,haloalkenylthio, haloalkynylthio, haloalkylamino, haloalkenylamino,haloalkynylamino, haloalkylsulfonyl, haloalkenylsulfonyl,haloalkynylsulfonyl, haloalkylcarbonyl, haloalkenylcarbonyl,haloalkynylcarbonyl, haloalkoxycarbonyl, haloalkenyloxycarbonyl,haloalkynyloxycarbonyl, haloalkylaminocarbonyl,haloalkenylaminocarbonyl, haloalkynylaminocarbonyl,haloalkoxycarbonylamino, haloalkenyloxycarbonylamino,haloalkynyloxycarbonylamino; cyano or nitro.

Furthermore, preferred compounds of the general formula 1 are thosewhere R³ is a radical of the general formula 2h-l ##STR7## where thesubstituents have the following meanings: R⁴ -R⁸ can be identical ordifferent and independently of one another are a low-molecular radicalselected from the group consisting of alkyl, alkenyl, alkynyl,cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, aryl,arylalkyl, arylalkenyl, arylalkynyl, hydroxyl, alkoxy, alkenyloxy,alkynyloxy, cycloalkoxy, cycloalkylalkoxy, cycloalkylalkenyloxy,cycloalkylalkynyloxy, aryloxy, arylalkoxy, arylalkenyloxy,arylalkynyloxy, thio, alkylthio, alkenylthio, alkynylthio,cycloalkylthio, cycloalkylalkylthio, cycloalkylalkenylthio,cycloalkylalkynylthio, arylthio, arylalkylthio, arylalkenylthio,arylalkynylthio, amino, unsubstituted or substituted mono- ordialkylamino, unsubstituted or substituted mono- or diarylamino,unsubstituted or substituted N-alkyl-N-arylamino, it being possible foralkyl and aryl to be identical or different, sulfonyl, alkylsulfonyl,cycloalkylsulfonyl, cycloalkylalkylsulfonyl, cycloalkylalkenylsulfonyl,cycloalkylalkynylsulfonyl, arylsulfonyl, arylalkylsulfonyl,arylalkenylsulfonyl, arylalkynylsulfonyl, sulfoxyl, alkylsulfoxyl,alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl,cycloalkylalkylsulfoxyl, cycloalkylalkenylsulfoxyl,cycloalkylalkynylsulfoxyl, arylsulfoxyl, arylalkylsulfoxyl,arylalkenylsulfoxyl, arylalkynylsulfoxyl, aminosulfonyl, unsubstitutedor substituted mono- or dialkylaminosulfonyl, unsubstituted orsubstituted mono- or diarylaminosulfonyl, unsubstituted or substitutedN-alkyl-N-arylaminosulfonyl, it being possible for alkyl and aryl to beidentical or different, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl,cycloalkylcarbonyl, cycloalkylalkylcarbonyl, cycloalkylalkenylcarbonyl,cycloalkylalkynylcarbonyl, arylcarbonyl, arylalkylcarbonyl,arylalkenylcarbonyl, arylalkynylcarbonyl, carboxyl, alkoxycarbonyl,alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl,cycloalkylalkoxycarbonyl, cycloalkylalkenyloxycarbonyl,cycloalkylalkynyloxycarbonyl, arylcarbonyl, arylalkoxycarbonyl,arylalkenyloxycarbonyl, arylalkynyloxycarbonyl, aminocarbonyl,unsubstituted or substituted mono- or dialkylaminocarbonyl,unsubstituted or substituted mono- or diarylaminocarbonyl, unsubstitutedor substituted N-alkyl-N-arylaminocarbonyl, it being possible for alkyland aryl to be identical or different, unsubstituted or substitutedmono- or dialkylcarbonylamino, unsubstituted or substituted mono- ordiarylcarbonylamino, unsubstituted or substitutedN-alkyl-N-arylcarbonylamino, it being possible for alkyl and aryl to beidentical or different, alkoxyaminocarbonyl, alkenyloxycarbonylamino,alkynyloxycarbonylamino, cycloalkoxycarbonylamino,cycloalkylalkoxycarbonylamino, cycloalkylalkenyloxycarbonylamino,cycloalkylalkynyloxycarbonylamino, aryloxycarbonylamino,arylalkoxycarbonylamino, arylalkenyloxycarbonylamino,arylalkynyloxycarbonylamino, halogen, haloalkyl, haloalkenyl,haloalkynyl, haloalkoxy, haloalkenyloxy, haloalkynyloxy, haloalkylthio,haloalkenylthio, haloalkynylthio, haloalkylamino, haloalkenylamino,haloalkynylamino, haloalkylsulfonyl, haloalkenylsulfonyl,haloalkynylsulfonyl, haloalkylcarbonyl, haloalkenylcarbonyl,haloalkynylcarbonyl, haloalkoxycarbonyl, haloalkenyloxycarbonyl,haloalkynyloxycarbonyl, haloalkylaminocarbonyl,haloalkenylaminocarbonyl, haloalkynylaminocarbonyl,haloalkoxycarbonylamino, haloalkenyloxycarbonylamino,haloalkynyloxycarbonylamino; hydroxy, cyano or nitro,

R⁴, R⁵ together can form a five- or six-membered, saturated orunsaturated, aromatic or non-aromatic, unsubstituted or mono- orpolysubstituted alkylene, alkenylene or alkdienylene chain;

R⁵, R⁶ together can form a five- or six-membered, saturated orunsaturated, aromatic or non-aromatic, unsubstituted or mono- orpolysubstituted alkylene, alkenylene or alkdienylene chain.

Moreover, preferred compounds of the general formula 1 are those whereR³ is a radical of the general formula 2, ##STR8## or a radical of thegeneral formula 2a-g ##STR9## or 2h-l ##STR10## where the substituentshave the following meanings: R⁴ -R⁸ can be identical or different andindependently of one another are hydrogen, C₁ -C₆ -alkyl, preferablymethyl, ethyl, propyl, 1-methylethyl, butyl, 2-methylpropyl, pentyl orhexyl; C₂ -C₆ -alkenyl, preferably ethenyl, 2-propenyl, 2-butenyl or3-butenyl; C₂ -C₆ -alkynyl, preferably ethynyl, 2-propynyl, 2-butynyl or3-butynyl; C₃ -C₆ -cycloalkyl, preferably cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl, C₃ -C₆ -cycloalkyl-C₁ -C₆ -alkyl, C₃ -C₆-cycloalkyl-C₂ -C₆ -alkenyl, C₃ -C₆ -cycloalkyl-C₂ -C₆ -alkynyl, aryl,preferably phenyl or naphthyl, aryl-C₁ -C₆ -alkyl, aryl-C₂ -C₆ -alkenyl,aryl-C₂ -C₆ -alkynyl; hydroxyl, C₁ -C₆ -alkoxy, preferably methyloxy,ethyloxy, propyloxy, 1-methylethyloxy, butyloxy, pentyloxy or hexyloxy,C₂ -C₆ -alkenyloxy, preferably ethenyloxy, 2-propenyloxy, 2-butenyloxyor 3-butenyloxy; C₂ -C₆ -alkynyloxy, preferably ethynyloxy,2-propynyloxy, 2-butynyloxy or 3-butynyloxy; C₃ -C₆ -cycloalkoxy,preferably cyclopropyloxy, cyclobutyloxy, cyclopentyloxy orcyclohexyloxy, C₃ -C₆ -cycloalkyl-C₁ -C₆ -alkoxy, C₃ -C₆ -cycloalkyl-C₂-C₆ -alkynyloxy; aryloxy, preferably phenoxy or naphthyloxy, aryl-C₁ -C₆-alkoxy, aryl-C₂ -C₆ -alkenyloxy, aryl-C₂ -C₆ -alkynyloxy; thio; C₁ -C₆-alkylthio, preferably methylthio, ethylthio, propylthio,1-methylethylthio, butylthio, pentylthio or hexylthio; C₂ -C₆-alkenylthio, preferably ethenylthio, 2-propenylthio, 2-butenylthio or3-butenylthio; C₂ -C₆ -alkynylthio, preferably ethynylthio,2-propynylthio, 2-butynylthio or 3-butynylthio; C₃ -C₆ -cycloalkylthio,preferably cyclopropylthio, cyclobutylthio, cyclopentylthio orcyclohexylthio, C₃ -C₆ -cycloalkyl-C₁ -C₆ -alkylthio, C₃ -C₆-cycloalkyl-C₂ -C₆ -alkenylthio, C₃ -C₆ -cycloalkyl-C₂ -C₆ -alkynylthio;arylthio, preferably phenylthio or naphthylthio, aryl-C₁ -C₆ -alkylthio,aryl-C₂ -C₆ -alkenylthio, aryl-C₂ -C₆ -alkynylthio; amino, unsubstitutedor substituted mono- or di-C₁ -C₆ -alkylamino, unsubstituted orsubstituted mono- or diarylamino, unsubstituted or substituted N-C₁ -C₆-alkyl-N-arylamino, it being possible for alkyl and aryl to be identicalor different; sulfonyl; C₁ -C₆ -alkylsulfonyl, preferablymethylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl,butylsulfonyl, 2-methylpropylsulfonyl, pentylsulfonyl or hexylsulfonyl;C₃ -C₆ -cycloalkylsulfonyl, preferably cyclopropylsulfonyl,cyclobutylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl, C₃ -C₆-cycloalkyl-C₁ -C₆ -alkylsulfonyl, C₃ -C₆ -cycloalkyl-C₂ -C₆-alkenylsulfonyl, C₃ -C₆ -cycloalkyl-C₂ -C₆ -alkynylsulfonyl;arylsulfonyl, preferably phenylsulfonyl or naphthylsulfonyl, aryl-C₁ -C₆-alkylsulfonyl, aryl-C₂ -C₆ -alkenylsulfonyl, aryl-C₂ -C₆-alkynylsulfonyl; sulfoxyl, C₁ -C₆ -alkylsulfoxyl, C₂ -C₆-alkenylsulfoxyl, C₂ -C₆ -alkynylsulfoxyl, C₃ -C₈ -cycloalkylsulfoxyl,C₃ -C₈ -cycloalkyl-C₁ -C₆ -alkylsulfoxyl, C₃ -C₈ -cycloalkyl-C₂ -C₆-alkenylsulfoxyl, C₃ -C₈ -cycloalkyl-C₂ -C₆ -alkynylsulfoxyl,arylsulfoxyl, aryl-C₁ -C₆ -alkylsulfoxyl, aryl-C₂ -C₆ -alkenylsulfoxyl,aryl-C₂ -C₆ -alkynylsulfoxyl, aminosulfonyl, unsubstituted orsubstituted mono- or di-C₁ -C₆ -alkylaminosulfonyl, unsubstituted orsubstituted mono- or diarylaminosulfonyl, unsubstituted or substitutedN-C₁ -C₆ -alkyl-N-arylaminosulfonyl, it being possible for alkyl andaryl to be identical or different, C₁ -C₆ -alkylcarbonyl, preferablymethylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl,butylcarbonyl, 2-methylpropylcarbonyl, pentylcarbonyl or hexylcarbonyl;C₂ -C₆ -alkenylcarbonyl, preferably ethenylcarbonyl, 2-propenylcarbonyl,2-butenylcarbonyl or 3-butenylcarbonyl; C₂ -C₆ -alkynylcarbonyl,preferably ethynylcarbonyl, 2-propynylcarbonyl, 2-butynylcarbonyl or3-butynylcarbonyl; C₃ -C₆ -cycloalkylcarbonyl, preferablycyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl orcyclohexylcarbonyl, C₃ -C₆ -cycloalkyl-C₁ -C₆ -alkylcarbonyl, C₃ -C₆-cycloalkyl-C₂ -C₆ -alkenylcarbonyl, C₃ -C₆ -cycloalkyl-C₂ -C₆-alkynylcarbonyl; arylcarbonyl, preferably phenylcarbonyl ornaphthylcarbonyl, aryl-C₁ -C₆ -alkylcarbonyl, aryl-C₂ -C₆-alkenylcarbonyl, aryl-C₂ -C₆ -alkynylcarbonyl; carboxyl; C₁ -C₆-alkoxycarbonyl, methyloxycarbonyl, ethyloxycarbonyl, propyloxycarbonyl,1-methylethyloxycarbonyl, butyloxycarbonyl, pentyloxycarbonyl orhexyloxycarbonyl, C₂ -C₆ -Alkenyloxycarbonyl, C₂ -C₆-alkynyloxycarbonyl, C₃ -C₆ -cycloalkoxycarbonyl,cyclopropyloxycarbonyl, cyclobutyloxycarbonyl, cyclopentyloxycarbonyl orcyclohexyloxycarbonyl, C₃ -C₆ -cycloalkyl-C₁ -C₆ -alkoxycarbonyl, C₃ -C₆-cycloalkyl-C₂ -C₆ -alkenyloxycarbonyl, C₃ -C₆ -cycloalkyl-C₂ -C₆-alkynyloxycarbonyl; aryloxycarbonyl, preferably phenyloxycarbonyl ornaphthyloxycarbonyl, aryl-C₁ -C₆ -alkoxycarbonyl, aryl-C₂ -C₆-alkenyloxycarbonyl, aryl-C₂ -C₆ -alkynyloxycarbonyl; aminocarbonyl;unsubstituted or substituted mono- or di-C₁ -C₆ -alkylaminocarbonyl,unsubstituted or substituted mono- or diarylaminocarbonyl, unsubstitutedor substituted N-C₁ -C₆ -alkyl-N-arylaminocarbonyl, it being possiblefor alkyl and aryl to be identical or different, unsubstituted orsubstituted mono- or di-C₁ -C₆ -alkylcarbonylamino, unsubstituted orsubstituted mono- or diarylcarbonylamino, unsubstituted or substitutedN-C₁ -C₆ -alkyl-N-arylcarbonylamino, it being possible for alkyl andaryl to be identical or different, C₁ -C₆ -alkoxyaminocarbonyl,preferably methyloxyaminocarbonyl, ethyloxyaminocarbonyl,propyloxyaminocarbonyl, 1-methylethyloxyaminocarbonyl,butyloxyaminocarbonyl, 2-methylpropyloxyaminocarbonyl,pentyloxyaminocarbonyl or hexyloxyaminocarbonyl; C₂ -C₆-alkenyloxycarbonylamino, preferably ethyleneoxyaminocarbonyl,2-propenyloxyaminocarbonyl, 2-butenyloxyaminocarbonyl or3-butenyloxyaminocarbonyl; C₂ -C₆ -alkynyloxycarbonylamino, preferablyethynyloxyaminocarbonyl, 2-propynyloxyaminocarbonyl,2-butynyloxyaminocarbonyl or 3-butynyloxyaminocarbonyl; C₃ -C₆-cycloalkoxy-aminocarbonyl, preferably cyclopropyloxyaminocarbonyl,cyclobutyloxyaminocarbonyl, cyclopentyloxyaminocarbonyl orcyclohexyloxyaminocarbonyl, C₃ -C₆ -cycloalkyl-C₁ -C₆-alkoxyaminocarbonyl, C₃ -C₆ -cycloalkyl-C₂ -C₆-alkenyloxyaminocarbonyl, C₃ -C₆ -cycloalkyl-C₁ -C₆-alkynyloxyaminocarbonyl; aryloxyaminocarbonyl, preferablyphenyloxyaminocarbonyl or naphthyloxyaminocarbonyl, aryl-C₁ -C₆-alkoxyaminocarbonylamino, aryl-C₂ -C₆ -alkenyloxyaminocarbonyl, aryl-C₂-C₆ -alkynyloxyaminocarbonyl; halogen, preferably fluorine, chlorine,bromine or iodine; C₁ -C₆ -haloalkyl, preferably chloromethyl,dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,2,2,2-trichloroethyl or pentafluoroethyl, C₂ -C₆ -haloalkenyl, C₂ -C₆-haloalkynyl; C₁ -C₆ -haloalkoxy, preferably chloromethyl,dichloromethyl, trichloromethyl, fluoromethyloxy, difluoromethyloxy,trifluoromethyloxy, chlorofluoromethyloxy, dichlorofluoromethyloxy,chlorodifluoromethyloxy, 1-fluoroethyloxy, 2-fluoroethyloxy,2,2-difluoroe-hyloxy, 2,2,2-trifluoroethyloxy,2-chloro-2-fluoroethyloxy, 2-chloro-2,2-difluoroethyloxy,2,2-dichloro-2-fluoroethyloxy, 2,2,2-trichloroethyloxy orpentafluoroethyloxy, C₂ -C₆ -haloalkenyloxy, C₂ -C₆ -haloalkynyloxy; C₁-C₆ -haloalkylthio, preferably chloromethylthio, dichloromethylthio,trichloromethylthio, fluoromethylthio, difluoromethylthio,trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio,chlorodifluoromethylthio, 1-fluoroethylthio, 2-fluoroethylthio,2,2-difluoroethylthio, 2,2,2-trifluoroethylthio,2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio,2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio orpentafluoroethylthio, C₂ -C₆ -haloalkenylthio, C₂ -C₆ -haloalkynylthio;C₁ -C₆ -haloalkylamino, preferably chloromethylamino,dichloromethylamino, trichloromethylamino, fluoromethylamino,difluoromethylamino, trifluoromethylamino, chlorofluoromethylamino,dichlorofluoromethylamino, chlorodifluoromethylamino,1-fluoroethylamino, 2-fluoroethylamino, 2,2-difluoroethylamino,2,2,2-trifluoroethylamino, 2-chloro-2-fluoroethyl-amino,2-chloro-2,2-difluoroethylamino, 2,2-dichloro-2-fluoroethylamino,2,2,2-trichloroethylamino or pentafluoroethylamino, C₂ -C₆-haloalkenylamino, C₂ -C₆ -haloalkynylamino, C₁ -C₆ -haloalkylsulfonyl,preferably chloromethylsulfonyl, dichloromethylsulfonyl,trichloromethylsulfonyl, fluoromethylsulfonyl, difluoromethylsulfonyl,trifluoromethylsulfonyl, chlorofluoromethylsulfonyl,dichlorofluoromethylsulfonyl, chlorodifluoromethylsulfonyl,1-fluoroethylsulfonyl, 2-fluoroethylsulfonyl, 2,2-difluoroethylsulfonyl,2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl,2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl,2,2,2-trichloroethylsulfonyl or pentafluoroethylsulfonyl, C₂ -C₆-haloalkenylsulfonyl, C₂ -C₆ -haloalkynylsulfonyl; C₁ -C₆-haloalkylcarbonyl, preferably chloromethylcarbonyl,dichloromethylcarbonyl, trichloromethylcarbonyl, fluoromethylcarbonyl,difluoromethylcarbonyl, trifluoromethylcarbonyl,chlorofluoromethylcarbonyl, dichlorofluoromethylcarbonyl,chlorodifluoromethylcarbonyl, 1-fluoroethylcarbonyl,2-fluoroethylcarbonyl, 2,2-difluoroethylcarbonyl,2,2,2-trifluoroethylcarbonyl, 2-chloro-2-fluoro-ethylcarbonyl,2-chloro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2-fluoro-ethylcarbonyl,2-2-2-trichloroethylcarbonyl or pentafluoroethylcarbonyl, C₂ -C₆-haloalkenylcarbonyl, C₂ -C₆ -haloalkynylcarbonyl; C₁ -C₆-haloalkoxycarbonyl, preferably chloromethyloxycarbonyl,dichloromethyloxycarbonyl, trichloromethyloxycarbonyl,fluoromethyloxycarbonyl, difluoromethyloxycarbonyl,trifluoromethyloxycarbonyl, chlorofluoromethyloxycarbonyl,dichlorofluoromethyloxycarbonyl, chlorodifluoromethyloxycarbonyl,1-fluoroethyloxycarbonyl, 2-fluoroethyloxycarbonyl,2,2-difluoroethyloxycarbonyl, 2,2,2-trifluoroethyloxycarbonyl,2-chloro-2-fluoroethyloxycarbonyl,2-chloro-2,2-difluoroethyloxycarbonyl,2,2-dichloro-2-fluoroethyloxycarbonyl, 2,2,2-trichloroethyloxycarbonylor pentafluoroethyloxycarbonyl, C₂ -C₆ -haloalkenyloxycarbonyl, C₂ -C₆-haloalkynyloxycarbonyl; C₁ -C₆ -haloalkylaminocarbonyl, preferablychloromethylaminocarbonyl, dichloromethylaminocarbonyl,trichloromethylaminocarbonyl, fluoromethylaminocarbonyl,difluoromethylaminocarbonyl, trifluoromethylaminocarbonyl,chlorofluoromethylaminocarbonyl, dichlorofluoromethylaminocarbonyl,chlorodlfluoromethylaminocarbonyl, 1-fluoroethylaminocarbonyl,2-fluoroethylaminocarbonyl, 2,2-difluoroethylaminocarbonyl,2,2,2-trifluoroethylaminocarbonyl, 2-chloro-2-fluoroethylaminocarbonyl,2-chloro-2,2-difluoroethylaminocarbonyl,2,2-dichloro-2-fluoroethylaminocarbonyl,2,2,2-trichloroethylaminocarbonyl or pentafluoroethylaminocarbonyl, C₂-C₆ -haloalkenylaminocarbonyl, C₂ -C₆ -haloalkynylaminocarbonyl; C₁ -C₆-haloalkoxycarbonylamino, chloromethyloxyaminocarbonyl,dichloromethyloxycarbonyl, trichloromethyloxyaminocarbonyl,fluoromethyloxyaminocarbonyl, difluoromethyloxyaminocarbonyl,trifluoromethyloxyaminocarbonyl, chlorofluoromethyloxyaminocarbonyl,dichlorofluoromethyloxyaminocarbonyl,chlorodifluoromethyloxyaminocarbonyl, 1-fluoroethyloxyaminocarbonyl,2-fluoroethyloxyaminocarbonyl, 2,2-difluoroethyloxyaminocarbonyl,2,2,2-trifluoroethyloxyaminocarbonyl,2-chloro-2-fluoroethyloxyaminocarbonyl,2-chloro-2,2-difluoroethyloxyaminocarbonyl,2,2-dichloro-2-fluoroethyloxyaminocarbonyl,2,2,2-trichloroethyloxyaminocarbonyl orpentafluoroethyloxyaminocarbonyl, C₂ -C₆ -haloalkenyloxycarbonylamino,C₂ -C₆ -haloalkynyloxycarbonylamino; cyano or nitro.

Moreover, especially preferred compounds of the general formula 1 arethose where R³ is a radical of the general formula 2b ##STR11## where R⁴and R⁶ are identical or different and independently of one another arealkyl, preferably methyl or ethyl, alkylsulfonyl, preferablymethylsulfonyl or ethylsulfonyl; halogen, preferably fluorine, chlorineor bromine, or haloalkyl, preferably difluoromethyl, trifluoromethyl,tetrafluoroethyl or trichloromethyl.

Also preferred compounds of the general formula 1 are those where R³ isa radical of the general formula 2h ##STR12## where R⁴, R⁵ and R⁶ areidentical or different and independently of one another are alkyl,preferably methyl or ethyl, alkoxy, preferably methoxy, ethoxy oraryloxy; alkylsulfonyl, preferably methylsulfonyl or ethylsulfonyl;halogen, preferably fluorine, chlorine, bromine or iodine; haloalkyl,preferably difluoromethyl, trifluoromethyl, tetrafluoroethyl ortrichloromethyl.

Also preferred compounds of the general formula 1 are those where R³ is2-chloro-4-sulfonylmethylphenyl.

Furthermore, also preferred compounds of the general formula 1 are thosewhere R³ is 2-sulfonylmethyl-4-trifluoromethylphenyl.

Also preferred compounds of the general formula 1 are those where R³ is2-chloro-3-methoxy-4-sulfonylmethylphenyl or2-chloro-3-ethoxy-4-sulfonylethylphenyl.

Also preferred compounds of the general formula 1 are those where thesubstituents are selected from a combination of the abovementionedpreferred substituents.

4-Benzoylisothiazoles of the general formula 1 are obtainable

a) by reacting the haloisothiazole compounds 3 ##STR13## where R¹ and R²have the above-described meanings and Y is halogen, preferably chlorine,bromine or iodine, with elemental magnesium or an organomagnesium ororganolithium compound and a carboxylic acid derivative of the generalformula 4 ##STR14## where R³ has the above-described meanings and R¹⁰ ishalogen, preferably chlorine, bromine or iodine, orN-alkoxy-N-alkylamino, preferably N-methoxy-N-methylamino or cyano,

at from -78° C. to 111° C., preferably at from -20° C. to 111° C., inthe presence of an inert solvent (A. Alberola, F. Alonso, P. Cuadrado,M. C. Sanudo, Synth. Commun. 17 (1987)1207), or

b. by reacting a halobenzene of the general formula 5 ##STR15## where R³has the above-described meanings and Y is halogen, preferably chlorine,bromine or iodine, with elemental magnesium or an organomagnesium ororganolithium compound and an isothiazolecarboxylic acid derivative ofthe general formula 6a or 6b, ##STR16## where X, R¹ and R² have theabove-described meanings and R¹⁰ is halogen, preferably chlorine,bromine or iodine, and N-alkoxy-N-alkylamino, preferablyN-methoxy-N-methylamino, at from -78° C. to 111° C., preferably at from-20° C. to 111° C., in the presence of an inert solvent (A. Alberola, F.Alonso, P Cuadrado, M. C. Sanudo, J. Heterocyclic Chem. 25 (1988) 235).

The haloisothiazole compounds 3 are synthesized by halogenatingisothiazole compounds of the general formula 7 ##STR17## where R¹ and R²have the above-described meanings by processes known from the literature(of which may be mentioned as representatives: a. A. Alberola, F.Alonso, P. Cuadrado, M. C. Sanudo, Synth. Commun. 17 (1987)1207; b.Vasilevskii, Izv. Akad. Nauk. SSSR Ser. Khim. (1975) 616).

Isothiazole compounds of the general formula 7 are known and aresynthesized following methods known from the literature (of which may bementioned as representatives: a. D. N NcGregor. U. Corbin, J. E. Swigor,I. C. Cheney, Tetrahedron 25 (1968) 389; b. F. Lucchesini, N. Picci. M.Pocci. Heterocycles 29 (1989) 97).

The isothiazolecarboxylic acid derivatives of the general formula 6b aresynthesized by reacting haloisothiazole compounds 3 with organiccyanides, for example copper(I) cyanide, by processes known from theliterature (of which may be mentioned as representatives: A. Alberola,F. Alonso, P Cuadrado, M. C. Sanudo, J. Heterocyclic Chem. 25 (1988)235). The corresponding isothiazolecarboxylic acid derivatives of thegeneral formula 6a can be obtained by processes known from theliterature starting from isothiazolecarboxylic acid derivatives of thegeneral formula 6b.

Preferred organomagnesium compounds are alkylmagnesium halides, forexample methyl- or ethylmagnesium bromide or methyl- or ethylmagnesiumchloride. Preferred organolithium compounds which are suitable arealiphatic lithium compounds such as lithium diisopropylamide,n-butyllithium or secondary-butyllithium.

The choice of organic solvent depends on the starting materialsemployed. In general, all inert solvents are suitable. Preferred inertsolvents are aliphatic, cyclic or acyclic ethers, eg. diethyl ether,tetrahydrofuran, dioxane or 1,2-dimethoxyethane. In addition, inertaromatic solvents such as benzene or toluene are also used.

The starting materials are normally reacted with each other instoichiometric amounts. However, it may be advantageous to employ one ofthe starting materials in an excess of 0.1 to 10 mol equivalents, forexample to improve the yield.

Examples of especially preferred compounds of the general formula 1 arecompiled in the tables which follow. The definitions of the radicals arenot only especially preferred in the specific combination of radicals,but also in each case by themselves.

                  TABLE 1                                                         ______________________________________                                                                       7                                               ##STR18##                                                                    No.          R.sup.4  R.sup.6                                                 ______________________________________                                        7.1          F        F                                                       7.2          F        Cl                                                      7.3          F        Br                                                      7.4          F        CH.sub.3                                                7.5          F        C.sub.2 H.sub.5                                         7.6          F        nC.sub.3 H.sub.7                                        7.7          F        iC.sub.3 H.sub.7                                        7.8          F        nC.sub.4 H.sub.9                                        7.9          F        tC.sub.4 H.sub.9                                        7.10         F        Ph                                                      7.11         F        OH                                                      7.12         F        OCH.sub.3                                               7.13         F        OC.sub.2 H.sub.5                                        7.14         F        O(nC.sub.3 H.sub.7)                                     7.15         F        O(iC.sub.3 H.sub.7)                                     7.16         F        O(nC.sub.4 H.sub.9)                                     7.17         F        O(tC.sub.4 H.sub.9)                                     7.18         F        OPh                                                     7.19         F        SH                                                      7.20         F        SCH.sub.3                                               7.21         F        SC.sub.2 H.sub.5                                        7.22         F        S(nC.sub.3 H.sub.7)                                     7.23         F        S(iC.sub.3 H.sub.7)                                     7.24         F        S(nC.sub.4 H.sub.9)                                     7.25         F        S(tC.sub.4 H.sub.9)                                     7.26         F        SPh                                                     7.27         F        CCl.sub.3                                               7.28         F        CH.sub.2 F                                              7.29         F        CHF.sub.2                                               7.30         F        CF.sub.3                                                7.31         F        CF.sub.2 CHF.sub.2                                      7.32         F        SO.sub.3 H                                              7.33         F        SO.sub.2 CH.sub.3                                       7.34         F        SO.sub.2 C.sub.2 H.sub.5                                7.35         F        SO.sub.2 (nC.sub.3 H.sub.7)                             7.36         F        SO.sub.2 (iC.sub.3 H.sub.7)                             7.37         F        SO.sub.2 (nC.sub.4 H.sub.9)                             7.38         F        SO.sub.2 (tC.sub.4 H.sub.9)                             7.39         F        SO.sub.2 Ph                                             7.40         F        NH.sub.2                                                7.41         F        NHCH.sub.3                                              7.42         F        NCH.sub.3 Ph                                            7.43         F        N(CH.sub.3)2                                            7.44         F        NPh.sub.2                                               7.45         F        CN                                                      7.46         F        NO.sub.2                                                7.47         Cl       F                                                       7.48         Cl       Cl                                                      7.49         Cl       Br                                                      7.50         Cl       CH.sub.3                                                7.51         Cl       C.sub.2 H.sub.5                                         7.53         Cl       nC.sub.3 H.sub.7                                        7.54         Cl       iC.sub.3 H.sub.7                                        7.55         Cl       nC.sub.4 H.sub.9                                        7.56         Cl       tC.sub.4 H.sub.9                                        7.57         Cl       Ph                                                      7.58         Cl       OH                                                      7.59         Cl       OCH.sub.3                                               7.60         Cl       OC.sub.2 H.sub.5                                        7.61         Cl       O(nC.sub.3 H.sub.7)                                     7.62         Cl       O(iC.sub.3 H.sub.7)                                     7.63         Cl       O(nC.sub.4 H.sub.9)                                     7.64         Cl       O(tC.sub.4 H.sub.9)                                     7.65         Cl       OPh                                                     7.66         Cl       SH                                                      7.67         Cl       SCH.sub.3                                               7.68         Cl       SC.sub.2 H.sub.5                                        7.69         Cl       S(nC.sub.3 H.sub.7)                                     7.70         Cl       S(iC.sub.3 H.sub.7)                                     7.71         Cl       S(nC.sub.4 H.sub.9)                                     7.72         Cl       S(tC.sub.4 H.sub.9)                                     7.73         Cl       SPh                                                     7.74         Cl       CCl.sub.3                                               7.75         Cl       CH.sub.2 F                                              7.76         Cl       CHF.sub.2                                               7.77         Cl       CF.sub.3                                                7.78         Cl       CF.sub.2 CHF.sub.2                                      7.79         Cl       SO.sub.3 H                                              7.80         Cl       SO.sub.2 CH.sub.3                                       7.81         Cl       SO.sub.2 C.sub.2 H.sub.5                                7.82         Cl       SO.sub.2 (nC.sub.3 H.sub.7)                             7.83         Cl       SO.sub.2 (iC.sub.3 H.sub.7)                             7.84         Cl       SO.sub.2 (nC.sub.4 H.sub.9)                             7.85         Cl       SO.sub.2 (tC.sub.4 H.sub.9)                             7.86         Cl       SO.sub.2 Ph                                             7.87         Cl       NH.sub.2                                                7.88         Cl       NHCH.sub.3                                              7.89         Cl       NCH.sub.3 Ph                                            7.90         Cl       N(CH.sub.3).sub.2                                       7.91         Cl       NPh.sub.2                                               7.92         Cl       CN                                                      7.93         Cl       NO.sub.2                                                7.94         CH.sub.3 F                                                       7.95         CH.sub.3 Cl                                                      7.98         CH.sub.3 Br                                                      7.97         CH.sub.3 CH.sub.3                                                7.98         CH.sub.3 C.sub.2 H.sub.5                                         7.99         CH.sub.3 nC.sub.3 H.sub.7                                        7.100        CH.sub.3 iC.sub.3 H.sub.7                                        7.101        CH.sub.3 nC.sub.4 H.sub.9                                        7.102        CH.sub.3 tC.sub.4 H.sub.9                                        7.102        CH.sub.3 Ph                                                      7.103        CH.sub.3 OH                                                      7.104        CH.sub.3 OCH.sub.3                                               7.105        CH.sub.3 OC.sub.2 H.sub.5                                        7.106        CH.sub.3 O(nC.sub.3 H.sub.7)                                     7.107        CH.sub.3 O(iC.sub.3 H.sub.7)                                     7.108        CH.sub.3 O(nC.sub.4 H.sub.9)                                     7.109        CH.sub.3 O(tC.sub.4 H.sub.9)                                     7.110        CH.sub.3 OPh                                                     7.111        CH.sub.3 SH                                                      7.112        CH.sub.3 SCH.sub.3                                               7.113        CH.sub.3 SC.sub.2 H.sub.5                                        7.114        CH.sub.3 S(nC.sub.3 H.sub.7)                                     7.115        CH.sub.3 S(iC.sub.3 H.sub.7)                                     7.116        CH.sub.3 S(nC.sub.4 H.sub.9)                                     7.117        CH.sub.3 S(tC.sub.4 H.sub.9)                                     7.118        CH.sub.3 SPh                                                     7.119        CH.sub.3 CCl.sub.3                                               7.120        CH.sub.3 CH.sub.2 F                                              7.121        CH.sub.3 CHF.sub.2                                               7.122        CH.sub.3 CF.sub.3                                                7.123        CH.sub.3 CF.sub.2 CHF.sub.2                                      7.124        CH.sub.3 SO.sub.3 H                                              7.125        CH.sub.3 SO.sub.2 CH.sub.3                                       7.126        CH.sub.3 SO.sub.2 C.sub.2 H.sub.5                                7.127        CH.sub.3 SO.sub.2 (nC.sub.3 H.sub.7)                             7.128        CH.sub.3 SO.sub.2 (iC.sub.3 H.sub.7)                             7.129        CH.sub.3 SO.sub.2 (nC.sub.4 H.sub.9)                             7.130        CH.sub.3 SO.sub.2 (tC.sub.4 H.sub.9)                             7.131        CH.sub.3 SO.sub.2 Ph                                             7.132        CH.sub.3 NH.sub.2                                                7.133        CH.sub.3 NHCH.sub.3                                              7.134        CH.sub.3 NCH.sub.3 Ph                                            7.135        CH.sub.3 N(CH.sub.3)2                                            7.136        CH.sub.3 NPh.sub.2                                               7.137        CH.sub.3 CN                                                      7.138        CH.sub.3 NO.sub.2                                                7.139        CF.sub.3 F                                                       7.140        CF.sub.3 Cl                                                      7.141        CF.sub.3 Br                                                      7.142        CF.sub.3 CH.sub.3                                                7.143        CF.sub.3 C.sub.2 H.sub.5                                         7.144        CF.sub.3 nC.sub.3 H.sub.7                                        7.145        CF.sub.3 iC.sub.3 H.sub.7                                        7.146        CF.sub.3 nC.sub.4 H.sub.9                                        7.147        CF.sub.3 tC.sub.4 H.sub.9                                        7.148        CF.sub.3 Ph                                                      7.149        CF.sub.3 OH                                                      7.150        CF.sub.3 OCH.sub.3                                               7.151        CF.sub.3 OC.sub.2 H.sub.5                                        7.152        CF.sub.3 O(nC.sub.3 H.sub.7)                                     7.153        CF.sub.3 O(iC.sub.3 H.sub.7)                                     7.154        CF.sub.3 O(nC.sub.4 H.sub.9)                                     7.155        CF.sub.3 O(tC.sub.4 H.sub.9)                                     7.156        CF.sub.3 OPh                                                     7.157        CF.sub.3 SH                                                      7.158        CF.sub.3 SCH.sub.3                                               7.159        CF.sub.3 SC.sub.2 H.sub.5                                        7.160        CF.sub.3 S(nC.sub.3 H.sub.7)                                     7.161        CF.sub.3 S(iC.sub.3 H.sub.7)                                     7.162        CF.sub.3 S(nC.sub.4 H.sub.9)                                     7.163        CF.sub.3 S(tC.sub.4 H.sub.9)                                     7.164        CF.sub.3 SPh                                                     7.165        CF.sub.3 CCl.sub.3                                               7.166        CF.sub.3 CH.sub.2 F                                              7.167        CF.sub.3 CHF.sub.2                                               7.168        CF.sub.3 CF.sub.3                                                7.169        CF.sub.3 CF.sub.2 CHF.sub.2                                      7.170        CF.sub.3 SO.sub.3 H                                              7.171        CF.sub.3 SO.sub.2 CH.sub.3                                       7.172        CF.sub.3 SO.sub.2 C.sub.2 H.sub.5                                7.173        CF.sub.3 SO.sub.2 (nC.sub.3 H.sub.7)                             7.174        CF.sub.3 SO.sub.2 (iC.sub.3 H.sub.7)                             7.175        CF.sub.3 SO.sub.2 (nC.sub.4 H.sub.9)                             7.176        CF.sub.3 SO.sub.2 (tC.sub.4 H.sub.9)                             7.177        CF.sub.3 SO.sub.2 Ph                                             7.178        CF.sub.3 NH.sub.2                                                7.179        CF.sub.3 NHCH.sub.3                                              7.180        CF.sub.3 NCH.sub.3 Ph                                            7.181        CF.sub.3 N(CH.sub.3).sub.2                                       7.182        CF.sub.3 NPh.sub.2                                               7.183        CF.sub.3 CN                                                      7.184        CF.sub.3 NO.sub.2                                                7.185        SO.sub.2 CH.sub.3                                                                      F                                                       7.186        SO.sub.2 CH.sub.3                                                                      Cl                                                      7.187        SO.sub.2 CH.sub.3                                                                      Br                                                      7.188        SO.sub.2 CH.sub.3                                                                      CH3                                                     7.189        SO.sub.2 CH.sub.3                                                                      C.sub.2 H.sub.5                                         7.190        SO.sub.2 CH.sub.3                                                                      nC.sub.3 H.sub.7                                        7.191        SO.sub.2 CH.sub.3                                                                      iC.sub.3 H.sub.7                                        7.192        SO.sub.2 CH.sub.3                                                                      nC.sub.4 H.sub.9                                        7.193        SO.sub.2 CH.sub.3                                                                      tC.sub.4 H.sub.9                                        7.194        SO.sub.2 CH.sub.3                                                                      Ph                                                      7.195        SO.sub.2 CH.sub.3                                                                      OH                                                      7.196        SO.sub.2 CH.sub.3                                                                      OCH.sub.3                                               7.197        SO.sub.2 CH.sub.3                                                                      OC.sub.2 H.sub.5                                        7.198        SO.sub.2 CH.sub.3                                                                      O(nC.sub.3 H.sub.7)                                     7.199        SO.sub.2 CH.sub.3                                                                      O(iC.sub.3 H.sub.7)                                     7.200        SO.sub.2 CH.sub.3                                                                      O(nC.sub.4 H.sub.9)                                     7.201        SO.sub.2 CH.sub.3                                                                      O(tC.sub.4 H.sub.9)                                     7.202        SO.sub.2 CH.sub.3                                                                      OPh                                                     7.203        SO.sub.2 CH.sub.3                                                                      SH                                                      7.204        SO.sub.2 CH.sub.3                                                                      SCH.sub.3                                               7.205        SO.sub.2 CH.sub.3                                                                      SC.sub.2 H.sub.5                                        7.206        SO.sub.2 CH.sub.3                                                                      S(nC.sub.3 H.sub.7)                                     7.207        SO.sub.2 CH.sub.3                                                                      S(iC.sub.3 H.sub.7)                                     7.208        SO.sub.2 CH.sub.3                                                                      S(nC.sub.4 H.sub.9)                                     7.209        SO.sub.2 CH.sub.3                                                                      S(tC.sub.4 H.sub.9)                                     7.210        SO.sub.2 CH.sub.3                                                                      SPh                                                     7.211        SO.sub.2 CH.sub.3                                                                      CCl.sub.3                                               7.212        SO.sub.2 CH.sub.3                                                                      CH.sub.2 F                                              7.213        SO.sub.2 CH.sub.3                                                                      CHF.sub.2                                               7.214        SO.sub.2 CH.sub.3                                                                      CF.sub.3                                                7.215        SO.sub.2 CH.sub.3                                                                      CF.sub.2 CHF.sub.2                                      7.216        SO.sub.2 CH.sub.3                                                                      SO.sub.3 H                                              7.217        SO.sub.2 CH.sub.3                                                                      SO.sub.2 CH.sub.3                                       7.218        SO.sub.2 CH.sub.3                                                                      SO.sub.2 C.sub.2 H.sub.5                                7.219        SO.sub.2 CH.sub.3                                                                      SO.sub.2 (nC.sub.3 H.sub.7)                             7.220        SO.sub.2 CH.sub.3                                                                      SO.sub.2 (iC.sub.3 H.sub.7)                             7.221        SO.sub.2 CH.sub.3                                                                      SO.sub.2 (nC.sub.4 H.sub.9)                             7.222        SO.sub.2 CH.sub.3                                                                      SO.sub.2 (tC.sub.4 H.sub.9)                             7.223        SO.sub.2 CH.sub.3                                                                      SO.sub.2 Ph                                             7.224        SO.sub.2 CH.sub.3                                                                      NH.sub.2                                                7.225        SO.sub.2 CH.sub.3                                                                      NHCH.sub.3                                              7.226        SO.sub.2 CH.sub.3                                                                      NCH.sub.3 Ph                                            7.227        SO.sub.2 CH.sub.3                                                                      N(CH.sub.3).sub.2                                       7.228        SO.sub.2 CH.sub.3                                                                      NPh.sub.2                                               7.229        SO.sub.2 CH.sub.3                                                                      CN                                                      7.230        SO.sub.2 CH.sub.3                                                                      NO.sub.2                                                7.231        CN       F                                                       7.232        CN       Cl                                                      7.233        CN       Br                                                      7.234        CN       CH.sub.3                                                7.235        CN       C.sub.2 H.sub.5                                         7.236        CN       nC.sub.3 H.sub.7                                        7.237        CN       iC.sub.3 H.sub.7                                        7.238        CN       nC.sub.4 H.sub.9                                        7.239        CN       tC.sub.4 H.sub.9                                        7.240        CN       Ph                                                      7.241        CN       OH                                                      7.242        CN       OCH.sub.3                                               7.243        CN       OC.sub.2 H.sub.5                                        7.244        CN       O(nC.sub.3 H.sub.7)                                     7.245        CN       O(iC.sub.3 H.sub.7)                                     7.246        CN       O(nC.sub.4 H.sub.9)                                     7.247        CN       O(tC.sub.4 H.sub.9)                                     7.248        CN       OPh                                                     7.249        CN       SH                                                      7.250        CN       SCH.sub.3                                               7.251        CN       SC.sub.2 H.sub.5                                        7.252        CN       S(nC.sub.3 H.sub.7)                                     7.253        CN       S(iC.sub.3 H.sub.7)                                     7.254        CN       S(nC.sub.4 H.sub.9)                                     7.255        CN       S(tC.sub.4 H.sub.9)                                     7.256        CN       SPh                                                     7.257        CN       CCl.sub.3                                               7.258        CN       CH.sub.2 F                                              7.259        CN       CHF.sub.2                                               7.260        CN       CF.sub.3                                                7.261        CN       CF.sub.2 CHF.sub.2                                      7.262        CN       SO.sub.3 H                                              7.263        CN       SO.sub.2 CH.sub.3                                       7.264        CN       SO.sub.2 C.sub.2 H.sub.5                                7.265        CN       SO.sub.2 (nC.sub.3 H.sub.7)                             7.266        CN       SO.sub.2 (iC.sub.3 H.sub.7)                             7.267        CN       SO.sub.2 (nC.sub.4 H.sub.9)                             7.268        CN       SO.sub.2 (tC.sub.4 H.sub.9)                             7.269        CN       SO.sub.2 Ph                                             7.270        CN       NH.sub.2                                                7.271        CN       NHCH.sub.3                                              7.272        CN       NCH.sub.3 Ph                                            7.273        CN       N(CH.sub.3).sub.2                                       7.274        CN       NPh.sub.2                                               7.275        CN       CN                                                      7.276        CN       NO.sub.2                                                ______________________________________                                    

                  TABLE 2                                                         ______________________________________                                                                       8                                               ##STR19##                                                                    No.     R.sup.4       R.sup.5 R.sup.6                                         ______________________________________                                        8.1     F             OCH.sub.3                                                                             F                                               8.2     F             OCH.sub.3                                                                             Cl                                              8.3     F             OCH.sub.3                                                                             Br                                              8.4     F             OCH.sub.3                                                                             CH.sub.3                                        8.5     F             OCH.sub.3                                                                             C.sub.2 H.sub.5                                 8.6     F             OCH.sub.3                                                                             nC.sub.3 H.sub.7                                8.7     F             OCH.sub.3                                                                             iC.sub.3 H.sub.7                                8.8     F             OCH.sub.3                                                                             nC.sub.4 H.sub.9                                8.9     F             OCH.sub.3                                                                             tC.sub.4 H.sub.9                                8.10    F             OCH.sub.3                                                                             Ph                                              8.11    F             OCH.sub.3                                                                             OH                                              8.12    F             OCH.sub.3                                                                             OCH.sub.3                                       8.13    F             OCH.sub.3                                                                             OC.sub.2 H.sub.5                                8.14    F             OCH.sub.3                                                                             O(nC.sub.3 H.sub.7)                             8.15    F             OCH.sub.3                                                                             O(iC.sub.3 H.sub.7)                             8.16    F             OCH.sub.3                                                                             O(nC.sub.4 H.sub.9)                             8.17    F             OCH.sub.3                                                                             O(tC.sub.4 H.sub.9)                             8.18    F             OCH.sub.3                                                                             OPh                                             8.19    F             OCH.sub.3                                                                             SH                                              8.20    F             OCH.sub.3                                                                             SCH.sub.3                                       8.21    F             OCH.sub.3                                                                             SC.sub.2 H.sub.5                                8.22    F             OCH.sub.3                                                                             S(nC.sub.3 H.sub.7)                             8.23    F             OCH.sub.3                                                                             S(iC.sub.3 H.sub.7)                             8.24    F             OCH.sub.3                                                                             S(nC.sub.4 H.sub.9)                             8.25    F             OCH.sub.3                                                                             S(tC.sub.4 H.sub.9)                             8.26    F             OCH.sub.3                                                                             SPh                                             8.27    F             OCH.sub.3                                                                             CCl.sub.3                                       8.28    F             OCH.sub.3                                                                             CH.sub.2 F                                      8.29    F             OCH.sub.3                                                                             CHF.sub.2                                       8.30    F             OCH.sub.3                                                                             CF.sub.3                                        8.31    F             OCH.sub.3                                                                             CF.sub.2 CHF.sub.2                              8.32    F             OCH.sub.3                                                                             SO.sub.3 H                                      8.33    F             OCH.sub.3                                                                             SO.sub.2 CH.sub.3                               8.34    F             OCH.sub.3                                                                             SO.sub.2 C.sub.2 H.sub.5                        8.35    F             OCH.sub.3                                                                             SO.sub.2 (nC.sub.3 H.sub.7)                     8.36    F             OCH.sub.3                                                                             SO.sub.2 (iC.sub.3 H.sub.7)                     8.37    F             OCH.sub.3                                                                             SO.sub.2 (nC.sub.4 H.sub.9)                     8.38    F             OCH.sub.3                                                                             SO.sub.2 (tC.sub.4 H.sub.9)                     8.39    F             OCH.sub.3                                                                             SO.sub.2 Ph                                     8.40    F             OCH.sub.3                                                                             NH.sub.2                                        8.41    F             OCH.sub.3                                                                             NHCH.sub.3                                      8.42    F             OCH.sub.3                                                                             NCH.sub.3 Ph                                    8.43    F             OCH.sub.3                                                                             N(CH.sub.3).sub.2                               8.44    F             OCH.sub.3                                                                             NPh.sub.2                                       8.45    F             OCH.sub.3                                                                             CN                                              8.46    F             OCH.sub.3                                                                             NO.sub.2                                        8.47    Cl            OCH.sub.3                                                                             F                                               8.48    Cl            OCH.sub.3                                                                             Cl                                              8.49    Cl            OCH.sub.3                                                                             Br                                              8.50    Cl            OCH.sub.3                                                                             CH.sub.3                                        8.51    Cl            OCH.sub.3                                                                             C.sub.2 H.sub.5                                 8.53    Cl            OCH.sub.3                                                                             nC.sub.3 H.sub.7                                8.54    Cl            OCH.sub.3                                                                             iC.sub.3 H.sub.7                                8.55    Cl            OCH.sub.3                                                                             nC.sub.4 H.sub.9                                8.56    Cl            OCH.sub.3                                                                             tC.sub.4 H.sub.9                                8.57    Cl            OCH.sub.3                                                                             Ph                                              8.58    Cl            OCH.sub.3                                                                             OH                                              8.59    Cl            OCH.sub.3                                                                             OCH.sub.3                                       8.60    Cl            OCH.sub.3                                                                             OC.sub.2 H.sub.5                                8.61    Cl            OCH.sub.3                                                                             O(nC.sub.3 H.sub.7)                             8.62    Cl            OCH.sub.3                                                                             O(iC.sub.3 H.sub.7)                             8.63    Cl            OCH.sub.3                                                                             O(nC.sub.4 H.sub.9)                             8.64    Cl            OCH.sub.3                                                                             O(tC.sub.4 H.sub.9)                             8.65    Cl            OCH.sub.3                                                                             OPh                                             8.66    Cl            OCH.sub.3                                                                             SH                                              8.67    Cl            OCH.sub.3                                                                             SCH.sub.3                                       8.68    Cl            OCH.sub.3                                                                             SC.sub.2 H.sub.5                                8.69    Cl            OCH.sub.3                                                                             S(nC.sub.3 H.sub.7)                             8.70    Cl            OCH.sub.3                                                                             S(iC.sub.3 H.sub.7)                             8.71    Cl            OCH.sub.3                                                                             S(nC.sub.4 H.sub.9)                             8.72    Cl            OCH.sub.3                                                                             S(tC.sub.4 H.sub.9)                             8.73    Cl            OCH.sub.3                                                                             SPh                                             8.74    Cl            OCH.sub.3                                                                             CCl.sub.3                                       875     Cl            OCH.sub.3                                                                             CH.sub.2 F                                      8.76    Cl            OCH.sub.3                                                                             CHF.sub.2                                       8.77    Cl            OCH.sub.3                                                                             CF.sub.3                                        8.78    Cl            OCH.sub.3                                                                             CF.sub.2 CHF.sub.2                              8.79    Cl            OCH.sub.3                                                                             SO.sub.3 H                                      8.80    Cl            OCH.sub.3                                                                             SO.sub.2 CH.sub.3                               8.81    Cl            OCH.sub.3                                                                             SO.sub.2 C.sub.2 H.sub.5                        8.82    Cl            OCH.sub.3                                                                             SO.sub.2 (nC.sub.3 H.sub.7)                     8.83    Cl            OCH.sub.3                                                                             SO.sub.2 (iC.sub.3 H.sub.7)                     8.84    Cl            OCH.sub.3                                                                             SO.sub.2 (nC.sub.4 H.sub.9)                     8.85    Cl            OCH.sub.3                                                                             SO.sub.2 (tC.sub.4 H.sub.9)                     8.86    Cl            OCH.sub.3                                                                             SO.sub.2 Ph                                     8.87    Cl            OCH.sub.3                                                                             NH.sub.2                                        8.88    Cl            OCH.sub.3                                                                             NHCH.sub.3                                      8.89    Cl            OCH.sub.3                                                                             NCH.sub.3 Ph                                    8.90    Cl            OCH.sub.3                                                                             N(CH.sub.3).sub.2                               8.91    Cl            OCH.sub.3                                                                             NPh.sub.2                                       8.92    Cl            OCH.sub.3                                                                             CN                                              8.93    Cl            OCH.sub.3                                                                             NO.sub.2                                        8.94    CH.sub.3      OCH.sub.3                                                                             F                                               8.95    CH.sub.3      OCH.sub.3                                                                             Cl                                              8.96    CH.sub.3      OCH.sub.3                                                                             Br                                              8.97    CH.sub.3      OCH.sub.3                                                                             CH.sub.3                                        8.98    CH.sub.3      OCH.sub.3                                                                             C.sub.2 H.sub.5                                 8.99    CH.sub.3      OCH.sub.3                                                                             nC.sub.3 H.sub.7                                8.100   CH.sub.3      OCH.sub.3                                                                             iC.sub.3 H.sub.7                                8.101   CH.sub.3      OCH.sub.3                                                                             nC.sub.4 H.sub.9                                8.102   CH.sub.3      OCH.sub.3                                                                             tC.sub.4 H.sub.9                                8.102   CH.sub.3      OCH.sub.3                                                                             Ph                                              8.103   CH.sub.3      OCH.sub.3                                                                             OH                                              8.104   CH.sub.3      OCH.sub.3                                                                             OCH.sub.3                                       8.105   CH.sub.3      OCH.sub.3                                                                             OC.sub.2 H.sub.5                                8.106   CH.sub.3      OCH.sub.3                                                                             O(nC.sub.3 H.sub.7)                             8.107   CH.sub.3      OCH.sub.3                                                                             O(iC.sub.3 H.sub.7)                             8.108   CH.sub.3      OCH.sub.3                                                                             O(nC.sub.4 H.sub.9)                             8.109   CH.sub.3      OCH.sub.3                                                                             O(tC.sub.4 H.sub.9)                             8.110   CH.sub.3      OCH.sub.3                                                                             OPh                                             8.111   CH.sub.3      OCH.sub.3                                                                             SH                                              8.112   CH.sub.3      OCH.sub.3                                                                             SCH.sub.3                                       8.113   CH.sub.3      OCH.sub.3                                                                             SC.sub.2 H.sub.5                                8.114   CH.sub.3      OCH.sub.3                                                                             S(nC.sub.3 H.sub.7)                             8.115   CH.sub.3      OCH.sub.3                                                                             S(iC.sub.3 H.sub.7)                             8.116   CH.sub.3      OCH.sub.3                                                                             S(nC.sub.4 H.sub.9)                             8.117   CH.sub.3      OCH.sub.3                                                                             S(tC.sub.4 H.sub.9)                             8.118   CH.sub.3      OCH.sub.3                                                                             SPh                                             8.119   CH.sub.3      OCH.sub.3                                                                             CCl.sub.3                                       8.120   CH.sub.3      OCH.sub.3                                                                             CH.sub.2 F                                      8.121   CH.sub.3      OCH.sub.3                                                                             CHF.sub.2                                       8.122   CH.sub.3      OCH.sub.3                                                                             CF.sub.3                                        8.123   CH.sub.3      OCH.sub.3                                                                             CF.sub.2 CHF.sub.2                              8.124   CH.sub.3      OCH.sub.3                                                                             SO.sub.3 H                                      8.125   CH.sub.3      OCH.sub.3                                                                             SO.sub.2 CH.sub.3                               8.126   CH.sub.3      OCH.sub.3                                                                             SO.sub.2 C.sub.2 H.sub.5                        8.127   CH.sub.3      OCH.sub.3                                                                             SO.sub.2 (nC.sub.3 H.sub.7)                     8.128   CH.sub.3      OCH.sub.3                                                                             SO.sub.2 (iC.sub.3 H.sub.7)                     8.129   CH.sub.3      OCH.sub.3                                                                             SO.sub.2 (nC.sub.4 H.sub.9)                     8.130   CH.sub.3      OCH.sub.3                                                                             SO.sub.2 (tC.sub.4 H.sub.9)                     8.131   CH.sub.3      OCH.sub.3                                                                             SO.sub.2 Ph                                     8.132   CH.sub.3      OCH.sub.3                                                                             NH.sub.2                                        8.133   CH.sub.3      OCH.sub.3                                                                             NHCH.sub.3                                      8.134   CH.sub.3      OCH.sub.3                                                                             NCH.sub.3 Ph                                    8.135   CH.sub.3      OCH.sub.3                                                                             N(CH.sub.3).sub.2                               8.136   CH.sub.3      OCH.sub.3                                                                             NPh.sub.2                                       8.137   CH.sub.3      OCH.sub.3                                                                             CN                                              8.138   CH.sub.3      OCH.sub.3                                                                             NO.sub.2                                        8.139   CF.sub.3      OCH.sub.3                                                                             F                                               8.140   CF.sub.3      OCH.sub.3                                                                             Cl                                              8.141   CF.sub.3      OCH.sub.3                                                                             Br                                              8.142   CF.sub.3      OCH.sub.3                                                                             CH.sub.3                                        8.143   CF.sub.3      OCH.sub.3                                                                             C.sub.2 H.sub.5                                 8.144   CF.sub.3      OCH.sub.3                                                                             nC.sub.3 H.sub.7                                8.145   CF.sub.3      OCH.sub.3                                                                             iC.sub.3 H.sub.7                                8.146   CF.sub.3      OCH.sub.3                                                                             nC.sub.4 H.sub.9                                8.147   CF.sub.3      OCH.sub.3                                                                             tC.sub.4 H.sub.9                                8.148   CF.sub.3      OCH.sub.3                                                                             Ph                                              8.149   CF.sub.3      OCH.sub.3                                                                             OH                                              8.150   CF.sub.3      OCH.sub.3                                                                             OCH.sub.3                                       8.151   CF.sub.3      OCH.sub.3                                                                             OC.sub.2 H.sub.5                                8.152   CF.sub.3      OCH.sub.3                                                                             O(nC.sub.3 H.sub.7)                             8.153   CF.sub.3      OCH.sub.3                                                                             O(iC.sub.3 H.sub.7)                             8.154   CF.sub.3      OCH.sub.3                                                                             O(nC.sub.4 H.sub.9)                             8.155   CF.sub.3      OCH.sub.3                                                                             O(tC.sub.4 H.sub.9)                             8.156   CF.sub.3      OCH.sub.3                                                                             OPh                                             8.157   CF.sub.3      OCH.sub.3                                                                             SH                                              8.158   CF.sub.3      OCH.sub.3                                                                             SCH.sub.3                                       8.159   CF.sub.3      OCH.sub.3                                                                             SC.sub.2 H.sub.5                                8.160   CF.sub.3      OCH.sub.3                                                                             S(nC.sub.3 H.sub.7)                             8.161   CF.sub.3      OCH.sub.3                                                                             S(iC.sub.3 H.sub.7)                             8.162   CF.sub.3      OCH.sub.3                                                                             S(nC.sub.4 H.sub.9)                             8.163   CF.sub.3      OCH.sub.3                                                                             S(tC.sub.4 H.sub.9)                             8.164   CF.sub.3      OCH.sub.3                                                                             SPh                                             8.165   CF.sub.3      OCH.sub.3                                                                             CCl.sub.3                                       8.166   CF.sub.3      OCH.sub.3                                                                             CH.sub.2 F                                      8.167   CF.sub.3      OCH.sub.3                                                                             CHF.sub.2                                       8.168   CF.sub.3      OCH.sub.3                                                                             CF.sub.3                                        8.169   CF.sub.3      OCH.sub.3                                                                             CF.sub.2 CHF.sub.2                              8.170   CF.sub.3      OCH.sub.3                                                                             SO.sub.3 H                                      8.171   CF.sub.3      OCH.sub.3                                                                             SO.sub.2 CH.sub.3                               8.172   CF.sub.3      OCH.sub.3                                                                             SO.sub.2 C.sub.2 H.sub.5                        8.173   CF.sub.3      OCH.sub.3                                                                             SO.sub.2 (nC.sub.3 H.sub.7)                     8.174   CF.sub.3      OCH.sub.3                                                                             SO.sub.2 (iC.sub.3 H.sub.7)                     7.175   CF.sub.3      OCH.sub.3                                                                             SO.sub.2 (nC.sub.4 H.sub.9)                     8.176   CF.sub.3      OCH.sub.3                                                                             SO.sub.2 (tC.sub.4 H.sub.9)                     8.177   CF.sub.3      OCH.sub.3                                                                             SO.sub.2 Ph                                     8.178   CF.sub.3      OCH.sub.3                                                                             NH.sub.2                                        8.179   CF.sub.3      OCH.sub.3                                                                             NHCH.sub.3                                      8.180   CF.sub.3      OCH.sub.3                                                                             NCH.sub.3 Ph                                    8.181   CF.sub.3      OCH.sub.3                                                                             N(CH.sub.3).sub.2                               8.182   CF.sub.3      OCH.sub.3                                                                             NPh.sub.2                                       8.183   CF.sub.3      OCH.sub.3                                                                             CN                                              8.184   CF.sub.3      OCH.sub.3                                                                             NO.sub.2                                        8.185   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             F                                               8.186   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             Cl                                              8.187   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             Br                                              8.188   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             CH.sub.3                                        8.189   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             C.sub.2 H.sub.5                                 8.190   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             nC.sub.3 H.sub.7                                8.191   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             iC.sub.3 H.sub.7                                8.192   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             nC.sub.4 H.sub.9                                8.193   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             tC.sub.4 H.sub.9                                8.194   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             Ph                                              8.195   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             OH                                              8.196   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             OCH.sub.3                                       8.197   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             OC.sub.2 H.sub.5                                8.198   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             O(nC.sub.3 H.sub.7)                             8.199   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             O(iC.sub.3 H.sub.7)                             8.200   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             O(nC.sub.4 H.sub.9)                             8.201   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             O(tC.sub.4 H.sub.9)                             8.202   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             OPh                                             8.203   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             SH                                              8.204   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             SCH.sub.3                                       8.205   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             SC.sub.2 H.sub.5                                8.206   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             S(nC.sub.3 H.sub.7)                             8.207   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             S(iC.sub.3 H.sub.7)                             7.208   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             S(nC.sub.4 H.sub.9)                             8.209   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             S(tC.sub.4 H.sub.9)                             8.210   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             SPh                                             8.211   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             CCl.sub.3                                       8.212   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             CH.sub.2 F                                      8.213   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             CHF.sub.2                                       8.214   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             CF.sub.3                                        8.215   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             CF.sub.2 CHF.sub.2                              8.216   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             SO.sub.3 H                                      8.217   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             SO.sub.2 CH.sub.3                               8.218   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             SO.sub.2 C.sub.2 H.sub.5                        8.219   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             SO.sub.2 (nC.sub.3 H.sub.7)                     8.220   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             SO.sub.2 (iC.sub.3 H.sub.7)                     8.221   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             SO.sub.2 (nC.sub.4 H.sub.9)                     8.222   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             SO.sub.2 (tC.sub.4 H.sub.9)                     8.223   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             SO.sub.2 Ph                                     8.224   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             NH.sub.2                                        8.225   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             NHCH.sub.3                                      8.226   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             NCH.sub.3 Ph                                    8.227   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             N(CH.sub.3).sub.2                               8.228   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             NPh.sub.2                                       8.229   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             CN                                              8.230   SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                                                             NO.sub.2                                        8.231   CN            OCH.sub.3                                                                             F                                               8.232   CN            OCH.sub.3                                                                             Cl                                              8.233   CN            OCH.sub.3                                                                             Br                                              8.234   CN            OCH.sub.3                                                                             CH.sub.3                                        8.235   CN            OCH.sub.3                                                                             C.sub.2 H.sub.5                                 8.236   CN            OCH.sub.3                                                                             nC.sub.3 H.sub.7                                8.237   CN            OCH.sub.3                                                                             iC.sub.3 H.sub.7                                8.238   CN            OCH.sub.3                                                                             nC.sub.4 H.sub.9                                8.239   CN            OCH.sub.3                                                                             tC.sub.4 H.sub.9                                8.240   CN            OCH.sub.3                                                                             Ph                                              8.241   CN            OCH.sub.3                                                                             OH                                              8.242   CN            OCH.sub.3                                                                             OCH.sub.3                                       8.243   CN            OCH.sub.3                                                                             OC.sub.2 H.sub.5                                8.244   CN            OCH.sub.3                                                                             O(nC.sub.3 H.sub.7)                             8.245   CN            OCH.sub.3                                                                             O(iC.sub.3 H.sub.7)                             8.246   CN            OCH.sub.3                                                                             O(nC.sub.4 H.sub.9)                             8.247   CN            OCH.sub.3                                                                             O(tC.sub.4 H.sub.9)                             8.248   CN            OCH.sub.3                                                                             OPh                                             8.249   CN            OCH.sub.3                                                                             SH                                              8.250   CN            OCH.sub.3                                                                             SCH.sub.3                                       8.251   CN            OCH.sub.3                                                                             SC.sub.2 H.sub.5                                8.252   CN            OCH.sub.3                                                                             S(nC.sub.3 H.sub.7)                             8.253   CN            OCH.sub.3                                                                             S(iC.sub.3 H.sub.7)                             8.254   CN            OCH.sub.3                                                                             S(nC.sub.4 H.sub.9)                             8.255   CN            OCH.sub.3                                                                             S(tC.sub.4 H.sub.9)                             8.258   CN            OCH.sub.3                                                                             SPh                                             8.257   CN            OCH.sub.3                                                                             CCl.sub.3                                       8.258   CN            OCH.sub.3                                                                             CH.sub.2 F                                      8.259   CN            OCH.sub.3                                                                             CHF.sub.2                                       8.260   CN            OCH.sub.3                                                                             CF.sub.3                                        8.261   CN            OCH.sub.3                                                                             CF.sub.2 CHF.sub.2                              8.262   CN            OCH.sub.3                                                                             SO.sub.3 H                                      8.263   CN            OCH.sub.3                                                                             SO.sub.2 CH.sub.3                               8.264   CN            OCH.sub.3                                                                             SO.sub.2 C.sub.2 H.sub.5                        8.265   CN            OCH.sub.3                                                                             SO.sub.2 (nC.sub.3 H.sub.7)                     8.266   CN            OCH.sub.3                                                                             SO.sub.2 (iC.sub.3 H.sub.7)                     8.267   CN            OCH.sub.3                                                                             SO.sub.2 (nC.sub.4 H.sub.9)                     8.268   CN            OCH.sub.3                                                                             SO.sub.2 (tC.sub.4 H.sub.9)                     8.269   CN            OCH.sub.3                                                                             SO.sub.2 Ph                                     8.270   CN            OCH.sub.3                                                                             NH.sub.2                                        8.271   CN            OCH.sub.3                                                                             NHCH.sub.3                                      8.272   CN            OCH.sub.3                                                                             NCH.sub.3 Ph                                    8.273   CN            OCH.sub.3                                                                             N(CH.sub.3).sub.2                               8.274   CN            OCH.sub.3                                                                             NPh.sub.2                                       8.275   CN            OCH.sub.3                                                                             CN                                              8.276   CN            OCH.sub.3                                                                             NO.sub.2                                        ______________________________________                                    

                  TABLE 3                                                         ______________________________________                                                                       9                                               ##STR20##                                                                    No.          R.sup.4       R.sup.6                                            ______________________________________                                        9.1          F             F                                                  9.2          F             Cl                                                 9.3          F             Br                                                 9.4          F             CH.sub.3                                           9.5          F             C.sub.2 H.sub.5                                    9.6          F             nC.sub.3 H.sub.9                                   9.7          F             iC.sub.3 H.sub.9                                   9.8          F             nC.sub.4 H.sub.9                                   9.9          F             tC.sub.4 H.sub.9                                   9.10         F             Ph                                                 9.11         F             OH                                                 9.12         F             OCH.sub.3                                          9.13         F             OC.sub.2 H.sub.5                                   9.14         F             O(nC.sub.3 H.sub.9)                                9.15         F             O(iC.sub.3 H.sub.9)                                9.16         F             O(nC.sub.4 H.sub.9)                                9.17         F             O(tC.sub.4 H.sub.9)                                9.18         F             OPh                                                9.19         F             SH                                                 9.20         F             SCH.sub.3                                          9.21         F             SC.sub.2 H.sub.5                                   9.22         F             S(nC.sub.3 H.sub.9)                                9.23         F             S(iC.sub.3 H.sub.9)                                9.24         F             S(nC.sub.4 H.sub.9)                                9.25         F             S(tC.sub.4 H.sub.9)                                9.26         F             SPh                                                9.27         F             CCl.sub.3                                          9.28         F             CH.sub.2 F                                         9.29         F             CHF.sub.2                                          9.30         F             CF.sub.3                                           9.31         F             CF.sub.2 CHF.sub.2                                 9.32         F             SO.sub.3 H                                         9.33         F             SO.sub.2 CH.sub.3                                  9.34         F             SO.sub.2 C.sub.2 H.sub.5                           9.35         F             SO.sub.2 (nC.sub.3 H.sub.9)                        9.36         F             SO.sub.2 (iC.sub.3 H.sub.9)                        9.37         F             SO.sub.2 (nC.sub.4 H.sub.9)                        9.38         F             SO.sub.2 (tC.sub.4 H.sub.9)                        9.39         F             SO.sub.2 Ph                                        9.40         F             NH.sub.2                                           9.41         F             NHCH.sub.3                                         9.42         F             NCH.sub.3 Ph                                       9.43         F             N(CH.sub.3).sub.2                                  9.44         F             NPh.sub.2                                          9.45         F             CN                                                 9.46         F             NO.sub.2                                           9.47         Cl            F                                                  9.48         Cl            Cl                                                 9.49         Cl            Br                                                 9.50         Cl            CH.sub.3                                           9.51         Cl            C.sub.2 H.sub.5                                    9.53         Cl            nC.sub.3 H.sub.9                                   9.54         Cl            iC.sub.3 H.sub.9                                   9.55         Cl            nC.sub.4 H.sub.9                                   9.56         Cl            tC.sub.4 H.sub.9                                   9.57         Cl            Ph                                                 9.58         Cl            OH                                                 9.59         Cl            OCH.sub.3                                          9.60         Cl            OC.sub.2 H.sub.5                                   9.61         Cl            O(nC.sub.3 H.sub.9)                                9.62         Cl            O(iC.sub.3 H.sub.9)                                9.63         Cl            O(nC.sub.4 H.sub.9)                                9.64         Cl            O(tC.sub.4 H.sub.9)                                9.65         Cl            OPh                                                9.66         Cl            SH                                                 9.67         Cl            SCH.sub.3                                          9.68         Cl            SC.sub.2 H.sub.5                                   9.69         Cl            S(nC.sub.3 H.sub.9)                                9.70         Cl            S(iC.sub.3 H.sub.9)                                9.71         Cl            S(nC.sub.4 H.sub.9)                                9.72         Cl            S(tC.sub.4 H.sub.9)                                9.73         Cl            SPh                                                9.74         Cl            CCl.sub.3                                          9.75         Cl            CH.sub.2 F                                         9.76         Cl            CHF.sub.2                                          9.77         Cl            CF.sub.3                                           9.78         Cl            CF.sub.2 CHF.sub.2                                 9.79         Cl            SO.sub.3 H                                         9.80         Cl            SO.sub.2 CH.sub.3                                  9.81         Cl            SO.sub.2 C.sub.2 H.sub.5                           9.82         Cl            SO.sub.2 (nC.sub.3 H.sub.9)                        9.83         Cl            SO.sub.2 (iC.sub.3 H.sub.9)                        9.84         Cl            SO.sub.2 (nC.sub.4 H.sub.9)                        9.85         Cl            SO.sub.2 (tC.sub.4 H.sub.9)                        9.86         Cl            SO.sub.2 Ph                                        9.87         Cl            NH.sub.2                                           9.88         Cl            NHCH.sub.3                                         9.89         Cl            NCH.sub.3 Ph                                       9.90         Cl            N(CH.sub.3).sub.2                                  9.91         Cl            NPh.sub.2                                          9.92         Cl            CN                                                 9.93         Cl            NO.sub.2                                           9.94         CH.sub.3      F                                                  9.95         CH.sub.3      Cl                                                 9.96         CH.sub.3      Br                                                 9.97         CH.sub.3      CH.sub.3                                           9.98         CH.sub.3      C.sub.2 H.sub.5                                    9.99         CH.sub.3      nC.sub.3 H.sub.9                                   9.100        CH.sub.3      iC.sub.3 H.sub.9                                   9.101        CH.sub.3      nC.sub.4 H.sub.9                                   9.102        CH.sub.3      tC.sub.4 H.sub.9                                   9.102        CH.sub.3      Ph                                                 9.103        CH.sub.3      OH                                                 9.104        CH.sub.3      OCH.sub.3                                          9.105        CH.sub.3      OC.sub.2 H.sub.5                                   9.106        CH.sub.3      O(nC.sub.3 H.sub.9)                                9.107        CH.sub.3      O(iC.sub.3 H.sub.9)                                9.108        CH.sub.3      O(nC.sub.4 H.sub.9)                                9.109        CH.sub.3      O(tC.sub.4 H.sub.9)                                9.110        CH.sub.3      OPh                                                9.111        CH.sub.3      SH                                                 9.112        CH.sub.3      SCH.sub.3                                          9.113        CH.sub.3      SC.sub.2 H.sub.5                                   9.114        CH.sub.3      S(nC.sub.3 H.sub.9)                                9.115        CH.sub.3      S(iC.sub.3 H.sub.9)                                9.116        CH.sub.3      S(nC.sub.4 H.sub.9)                                9.117        CH.sub.3      S(tC.sub.4 H.sub.9)                                9.118        CH.sub.3      SPh                                                9.119        CH.sub.3      CCl.sub.3                                          9.120        CH.sub.3      CH.sub.2 F                                         9.121        CH.sub.3      CHF.sub.2                                          9.122        CH.sub.3      CF.sub.3                                           9.123        CH.sub.3      CF.sub.2 CHF.sub.2                                 9.124        CH.sub.3      SO.sub.3 H                                         9.125        CH.sub.3      SO.sub.2 CH.sub.3                                  9.126        CH.sub.3      SO.sub.2 C.sub.2 H.sub.5                           9.127        CH.sub.3      SO.sub.2 (nC.sub.3 H.sub.9)                        9.128        CH.sub.3      SO.sub.2 (iC.sub.3 H.sub.9)                        9.129        CH.sub.3      SO.sub.2 (nC.sub.4 H.sub.9)                        9.130        CH.sub.3      SO.sub.2 (tC.sub.4 H.sub.9)                        9.131        CH.sub.3      SO.sub.2 Ph                                        9.132        CH.sub.3      NH.sub.2                                           9.133        CH.sub.3      NHCH.sub.3                                         9.134        CH.sub.3      NCH.sub.3 Ph                                       9.135        CH.sub.3      N(CH.sub.3).sub.2                                  9.136        CH.sub.3      NPh.sub.2                                          9.137        CH.sub.3      CN                                                 9.138        CH.sub.3      NO.sub.2                                           9.139        CF.sub.3      F                                                  9.140        CF.sub.3      Cl                                                 9.141        CF.sub.3      Br                                                 9.142        CF.sub.3      CH.sub.3                                           9.143        CF.sub.3      C.sub.2 H.sub.5                                    9.144        CF.sub.3      nC.sub.3 H.sub.9                                   9.145        CF.sub.3      iC.sub.3 H.sub.9                                   9.146        CF.sub.3      nC.sub.4 H.sub.9                                   9.147        CF.sub.3      tC.sub.4 H.sub.9                                   9.148        CF.sub.3      Ph                                                 9.149        CF.sub.3      OH                                                 9.150        CF.sub.3      OCH.sub.3                                          9.151        CF.sub.3      OC.sub.2 H.sub.5                                   9.152        CF.sub.3      O(nC.sub.3 H.sub.9)                                9.153        CF.sub.3      O(iC.sub.3 H.sub.9)                                9.154        CF.sub.3      O(nC.sub.4 H.sub.9)                                9.155        CF.sub.3      O(tC.sub.4 H.sub.9)                                9.156        CF.sub.3      OPh                                                9.157        CF.sub.3      SH                                                 9.158        CF.sub.3      SCH.sub.3                                          9.159        CF.sub.3      SC.sub.2 H.sub.5                                   9.160        CF.sub.3      S(nC.sub.3 H.sub.9)                                9.161        CF.sub.3      S(iC.sub.3 H.sub.9)                                9.162        CF.sub.3      S(nC.sub.4 H.sub.9)                                9.163        CF.sub.3      S(tC.sub.4 H.sub.9)                                9.164        CF.sub.3      SPh                                                9.165        CF.sub.3      CCl.sub.3                                          9.166        CF.sub.3      CH.sub.2 F                                         9.167        CF.sub.3      CHF.sub.2                                          9.168        CF.sub.3      CF.sub.3                                           9.169        CF.sub.3      CF.sub.2 CHF.sub.2                                 9.170        CF.sub.3      SO.sub.3 H                                         9.171        CF.sub.3      SO.sub.2 CH.sub.3                                  9.172        CF.sub.3      SO.sub.2 C.sub.2 H.sub.5                           9.173        CF.sub.3      SO.sub.2 (nC.sub.3 H.sub.9)                        9.174        CF.sub.3      SO.sub.2 (iC.sub.3 H.sub.9)                        9.175        CF.sub.3      SO.sub.2 (nC.sub.4 H.sub.9)                        9.176        CF.sub.3      SO.sub.2 (tC.sub.4 H.sub.9)                        9.177        CF.sub.3      SO.sub.2 Ph                                        9.178        CF.sub.3      NH.sub.2                                           9.179        CF.sub.3      NHCH.sub.3                                         9.180        CF.sub.3      NCH.sub.3 Ph                                       9.181        CF.sub.3      N(CH.sub.3).sub.2                                  9.182        CF.sub.3      NPh.sub.2                                          9.183        CF.sub.3      CN                                                 9.184        CF.sub.3      NO.sub.2                                           9.185        SO.sub.2 CH.sub.3                                                                           F                                                  9.186        SO.sub.2 CH.sub.3                                                                           Cl                                                 9.187        SO.sub.2 CH.sub.3                                                                           Br                                                 9.188        SO.sub.2 CH.sub.3                                                                           CH.sub.3                                           9.189        SO.sub.2 CH.sub.3                                                                           C.sub.2 H.sub.5                                    9.190        SO.sub.2 CH.sub.3                                                                           nC.sub.3 H.sub.9                                   9.191        SO.sub.2 CH.sub.3                                                                           iC.sub.3 H.sub.9                                   9.192        SO.sub.2 CH.sub.3                                                                           nC.sub.4 H.sub.9                                   9.193        SO.sub.2 CH.sub.3                                                                           tC.sub.4 H.sub.9                                   9.194        SO.sub.2 CH.sub.3                                                                           Ph                                                 9.195        SO.sub.2 CH.sub.3                                                                           OH                                                 9.196        SO.sub.2 CH.sub.3                                                                           OCH.sub.3                                          9.197        SO.sub.2 CH.sub.3                                                                           OC.sub.2 H.sub.5                                   9.198        SO.sub.2 CH.sub.3                                                                           O(nC.sub.3 H.sub.9)                                9.199        SO.sub.2 CH.sub.3                                                                           O(iC.sub.3 H.sub.9)                                9.200        SO.sub.2 CH.sub.3                                                                           O(nC.sub.4 H.sub.9)                                9.201        SO.sub.2 CH.sub.3                                                                           O(tC.sub.4 H.sub.9)                                9.202        SO.sub.2 CH.sub.3                                                                           OPh                                                9.203        SO.sub.2 CH.sub.3                                                                           SH                                                 9.204        SO.sub.2 CH.sub.3                                                                           SCH.sub.3                                          9.205        SO.sub.2 CH.sub.3                                                                           SC.sub.2 H.sub.5                                   9.206        SO.sub.2 CH.sub.3                                                                           S(nC.sub.3 H.sub.9)                                9.207        SO.sub.2 CH.sub.3                                                                           S(iC.sub.3 H.sub.9)                                9.208        SO.sub.2 CH.sub.3                                                                           S(nC.sub.4 H.sub.9)                                9.209        SO.sub.2 CH.sub.3                                                                           S(tC.sub.4 H.sub.9)                                9.210        SO.sub.2 CH.sub.3                                                                           SPh                                                9.211        SO.sub.2 CH.sub.3                                                                           CCl.sub.3                                          9.212        SO.sub.2 CH.sub.3                                                                           CH.sub.2 F                                         9.213        SO.sub.2 CH.sub.3                                                                           CHF.sub.2                                          9.214        SO.sub.2 CH.sub.3                                                                           CF.sub.3                                           9.215        SO.sub.2 CH.sub.3                                                                           CF.sub.2 CHF.sub.2                                 9.216        SO.sub.2 CH.sub.3                                                                           SO.sub.3 H                                         9.217        SO.sub.2 CH.sub.3                                                                           SO.sub.2 CH.sub.3                                  9.218        SO.sub.2 CH.sub.3                                                                           SO.sub.2 C.sub.2 H.sub.5                           9.219        SO.sub.2 CH.sub.3                                                                           SO.sub.2 (nC.sub.3 H.sub.9)                        9.220        SO.sub.2 CH.sub.3                                                                           SO.sub.2 (iC.sub.3 H.sub.9)                        9.221        SO.sub.2 CH.sub.3                                                                           SO.sub.2 (nC.sub.4 H.sub.9)                        9.222        SO.sub.2 CH.sub.3                                                                           SO.sub.2 (tC.sub.4 H.sub.9)                        9.223        SO.sub.2 CH.sub.3                                                                           SO.sub.2 Ph                                        9.224        SO.sub.2 CH.sub.3                                                                           NH.sub.2                                           9.225        SO.sub.2 CH.sub.3                                                                           NHCH.sub.3                                         9.226        SO.sub.2 CH.sub.3                                                                           NCH.sub.3 Ph                                       9.227        SO.sub.2 CH.sub.3                                                                           N(CH.sub.3).sub.2                                  9.228        SO.sub.2 CH.sub.3                                                                           NPh.sub.2                                          9.229        SO.sub.2 CH.sub.3                                                                           CN                                                 9.230        SO.sub.2 CH.sub.3                                                                           NO.sub.2                                           9.231        CN            F                                                  9.232        CN            Cl                                                 9.233        CN            Br                                                 9.234        CN            CH.sub.3                                           9.235        CN            C.sub.2 H.sub.5                                    9.236        CN            nC.sub.3 H.sub.9                                   9.237        CN            iC.sub.3 H.sub.9                                   9.238        CN            nC.sub.4 H.sub.9                                   9.239        CN            tC.sub.4 H.sub.9                                   9.240        CN            Ph                                                 9.241        CN            OH                                                 9.242        CN            OCH.sub.3                                          9.243        CN            OC.sub.2 H.sub.5                                   9.244        CN            O(nC.sub.3 H.sub.9)                                9.245        CN            O(iC.sub.3 H.sub.9)                                9.246        CN            O(nC.sub.4 H.sub.9)                                9.247        CN            O(tC.sub.4 H.sub.9)                                9.248        CN            OPh                                                9.249        CN            SH                                                 9.250        CN            SCH.sub.3                                          9.251        CN            SC.sub.2 H.sub.5                                   9.252        CN            S(nC.sub.3 H.sub.9)                                9.253        CN            S(iC.sub.3 H.sub.9)                                9.254        CN            S(nC.sub.4 H.sub.9)                                9.255        CN            S(tC.sub.4 H.sub.9)                                9.256        CN            SPh                                                9.257        CN            CCl.sub.3                                          9.258        CN            CH.sub.2 F                                         9.259        CN            CHF.sub.2                                          9.260        CN            CF.sub.3                                           9.261        CN            CF.sub.2 CHF.sub.2                                 9.262        CN            SO.sub.3 H                                         9.263        CN            SO.sub.2 CH.sub.3                                  9.264        CN            SO.sub.2 C.sub.2 H.sub.5                           9.265        CN            SO.sub.2 (nC.sub.3 H.sub.9)                        9.266        CN            SO.sub.2 (iC.sub.3 H.sub.9)                        9.267        CN            SO.sub.2 (nC.sub.4 H.sub.9)                        9.268        CN            SO.sub.2 (tC.sub.4 H.sub.9)                        9.269        CN            SO.sub.2 Ph                                        9.270        CN            NH.sub.2                                           9.271        CN            NHCH.sub.3                                         9.272        CN            NCH.sub.3 Ph                                       9.273        CN            N(CH.sub.3).sub.2                                  9.274        CN            NPh.sub.2                                          9.275        CN            CN                                                 9.276        CN            NO.sub.2                                           ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                                                       10                                              ##STR21##                                                                    No.        R.sup.4    R.sup.5   R.sup.6                                       ______________________________________                                        10.1       F          OCH.sub.3 F                                             10.2       F          OCH.sub.3 Cl                                            10.3       F          OCH.sub.3 Br                                            10.4       F          OCH.sub.3 CH.sub.3                                      10.5       F          OCH.sub.3 C.sub.2 H.sub.5                               10.6       F          OCH.sub.3 nC.sub.3 H.sub.7                              10.7       F          OCH.sub.3 iC.sub.3 H.sub.7                              10.8       F          OCH.sub.3 nC.sub.4 H.sub.9                              10.9       F          OCH.sub.3 tC.sub.4 H.sub.9                              10.10      F          OCH.sub.3 Ph                                            10.11      F          OCH.sub.3 OH                                            10.12      F          OCH.sub.3 OCH.sub.3                                     10.13      F          OCH.sub.3 OC.sub.2 H.sub.5                              10.14      F          OCH.sub.3 O(nC.sub.3 H.sub.7)                           10.15      F          OCH.sub.3 O(iC.sub.3 H.sub.7)                           10.16      F          OCH.sub.3 O(nC.sub.4 H.sub.9)                           10.17      F          OCH.sub.3 O(tC.sub.4 H.sub.9)                           10.18      F          OCH.sub.3 OPh                                           10.19      F          OCH.sub.3 SH                                            10.20      F          OCH.sub.3 SCH.sub.3                                     10.21      F          OCH.sub.3 SC.sub.2 H.sub.5                              10.22      F          OCH.sub.3 S(nC.sub.3 H.sub.7)                           10.23      F          OCH.sub.3 S(iC.sub.3 H.sub.7)                           10.24      F          OCH.sub.3 S(nC.sub.4 H.sub.9)                           10.25      F          OCH.sub.3 S(tC.sub.4 H.sub.9)                           10.26      F          OCH.sub.3 SPh                                           10.27      F          OCH.sub.3 CCl.sub.3                                     10.28      F          OCH.sub.3 CH.sub.2 F                                    10.29      F          OCH.sub.3 CHF.sub.2                                     10.30      F          OCH.sub.3 CF.sub.3                                      10.31      F          OCH.sub.3 CF.sub.2 CHF.sub.2                            10.32      F          OCH.sub.3 SO.sub.3 H                                    10.33      F          OCH.sub.3 SO.sub.2 CH.sub.3                             10.34      F          OCH.sub.3 SO.sub.2 C.sub.2 H.sub.5                      10.35      F          OCH.sub.3 SO.sub.2 (nC.sub.3 H.sub.7)                   10.36      F          OCH.sub.3 SO.sub.2 (iC.sub.3 H.sub.7)                   10.37      F          OCH.sub.3 SO.sub.2 (nC.sub.4 H.sub.9)                   10.38      F          OCH.sub.3 SO.sub.2 (tC.sub.4 H.sub.9)                   10.39      F          OCH.sub.3 SO.sub.2 Ph                                   10.40      F          OCH.sub.3 NH.sub.2                                      10.41      F          OCH.sub.3 NHCH.sub.3                                    10.42      F          OCH.sub.3 NCH.sub.3 Ph                                  10.43      F          OCH.sub.3 N(CH.sub.3).sub.2                             10.44      F          OCH.sub.3 NPh.sub.2                                     10.45      F          OCH.sub.3 CN                                            10.46      F          OCH.sub.3 NO.sub.2                                      10.47      Cl         OCH.sub.3 F                                             10.48      Cl         OCH.sub.3 Cl                                            10.49      Cl         OCH.sub.3 Br                                            10.50      Cl         OCH.sub.3 CH.sub.3                                      10.51      Cl         OCH.sub.3 C.sub.2 H.sub.5                               10.53      Cl         OCH.sub.3 nC.sub.3 H.sub.7                              10.54      Cl         OCH.sub.3 iC.sub.3 H.sub.7                              10.55      Cl         OCH.sub.3 nC.sub.4 H.sub.9                              10.56      Cl         OCH.sub.3 tC.sub.4 H.sub.9                              10.57      Cl         OCH.sub.3 Ph                                            10.58      Cl         OCH.sub.3 OH                                            10.59      Cl         OCH.sub.3 OCH.sub.3                                     10.60      Cl         OCH.sub.3 OC.sub.2 H.sub.5                              10.61      Cl         OCH.sub.3 O(nC.sub.3 H.sub.7)                           10.62      Cl         OCH.sub.3 O(iC.sub.3 H.sub.7)                           10.63      Cl         OCH.sub.3 O(nC.sub.4 H.sub.9)                           10.64      Cl         OCH.sub.3 O(tC.sub.4 H.sub.9)                           10.65      Cl         OCH.sub.3 OPh                                           10.66      Cl         OCH.sub.3 SH                                            10.67      Cl         OCH.sub.3 SCH.sub.3                                     10.68      Cl         OCH.sub.3 SC.sub.2 H.sub.5                              10.69      Cl         OCH.sub.3 S(nC.sub.3 H.sub.7)                           10.70      Cl         OCH.sub.3 S(iC.sub.3 H.sub.7)                           10.71      Cl         OCH.sub.3 S(nC.sub.4 H.sub.9)                           10.72      Cl         OCH.sub.3 S(tC.sub.4 H.sub.9)                           10.73      Cl         OCH.sub.3 SPh                                           10.74      Cl         OCH.sub.3 CCl.sub.3                                     10.75      Cl         OCH.sub.3 CH.sub.2 F                                    10.76      Cl         OCH.sub.3 CHF.sub.2                                     10.77      Cl         OCH.sub.3 CF.sub.3                                      10.78      Cl         OCH.sub.3 CF.sub.2 CHF.sub.2                            10.79      Cl         OCH.sub.3 SO.sub.3 H                                    10.80      Cl         OCH.sub.3 SO.sub.2 CH.sub.3                             10.81      Cl         OCH.sub.3 SO.sub.2 C.sub.2 H.sub.5                      10.82      Cl         OCH.sub.3 SO.sub.2 (nC.sub.3 H.sub.7)                   10.83      Cl         OCH.sub.3 SO.sub.2 (iC.sub.3 H.sub.7)                   10.84      Cl         OCH.sub.3 SO.sub.2 (nC.sub.4 H.sub.9)                   10.85      Cl         OCH.sub.3 SO.sub.2 (tC.sub.4 H.sub.9)                   10.86      Cl         OCH.sub.3 SO.sub.2 Ph                                   10.87      Cl         OCH.sub.3 NH.sub.2                                      10.88      Cl         OCH.sub.3 NHCH.sub.3                                    10.89      Cl         OCH.sub.3 NCH.sub.3 Ph                                  10.90      Cl         OCH.sub.3 N(CH.sub.3).sub.2                             10.91      Cl         OCH.sub.3 NPh.sub.2                                     10.92      Cl         OCH.sub.3 CN                                            10.93      Cl         OCH.sub.3 NO.sub.2                                      10.94      CH.sub.3   OCH.sub.3 F                                             10.95      CH.sub.3   OCH.sub.3 Cl                                            10.96      CH.sub.3   OCH.sub.3 Br                                            10.97      CH.sub.3   OCH.sub.3 CH.sub.3                                      10.98      CH.sub.3   OCH.sub.3 C.sub.2 H.sub.5                               10.99      CH.sub.3   OCH.sub.3 nC.sub.3 H.sub.7                              10.100     CH.sub.3   OCH.sub.3 iC.sub.3 H.sub.7                              10.101     CH.sub.3   OCH.sub.3 nC.sub.4 H.sub.9                              10.102     CH.sub.3   OCH.sub.3 tC.sub.4 H.sub.9                              10.102     CH.sub.3   OCH.sub.3 Ph                                            10.103     CH.sub.3   OCH.sub.3 OH                                            10.104     CH.sub.3   OCH.sub.3 OCH.sub.3                                     10.105     CH.sub.3   OCH.sub.3 OC.sub.2 H.sub.5                              10.106     CH.sub.3   OCH.sub.3 O(nC.sub.3 H.sub.7)                           10.107     CH.sub.3   OCH.sub.3 O(iC.sub.3 H.sub.7)                           10.108     CH.sub.3   OCH.sub.3 O(nC.sub.4 H.sub.9)                           10.109     CH.sub.3   OCH.sub.3 O(tC.sub.4 H.sub.9)                           10.110     CH.sub.3   OCH.sub.3 OPh                                           10.111     CH.sub.3   OCH.sub.3 SH                                            10.112     CH.sub.3   OCH.sub.3 SCH.sub.3                                     10.113     CH.sub.3   OCH.sub.3 SC.sub.2 H.sub.5                              10.114     CH.sub.3   OCH.sub.3 S(nC.sub.3 H.sub.7)                           10.115     CH.sub.3   OCH.sub.3 S(iC.sub.3 H.sub.7)                           10.116     CH.sub.3   OCH.sub.3 S(nC.sub.4 H.sub.9)                           10.117     CH.sub.3   OCH.sub.3 S(tC.sub.4 H.sub.9)                           10.118     CH.sub.3   OCH.sub.3 SPh                                           10.119     CH.sub.3   OCH.sub.3 CCl.sub.3                                     10.120     CH.sub.3   OCH.sub.3 CH.sub.2 F                                    10.121     CH.sub.3   OCH.sub.3 CHF.sub.2                                     10.122     CH.sub.3   OCH.sub.3 CF.sub.3                                      10.123     CH.sub.3   OCH.sub.3 CF.sub.2 CHF.sub.2                            10.124     CH.sub.3   OCH.sub.3 SO.sub.3 H                                    10.125     CH.sub.3   OCH.sub.3 SO.sub.2 CH.sub.3                             10.126     CH.sub.3   OCH.sub.3 SO.sub.2 C.sub.2 H.sub.5                      10.127     CH.sub.3   OCH.sub.3 SO.sub.2 (nC.sub.3 H.sub.7)                   10.128     CH.sub.3   OCH.sub.3 SO.sub.2 (iC.sub.3 H.sub.7)                   10.129     CH.sub.3   OCH.sub.3 SO.sub.2 (nC.sub.4 H.sub.9)                   10.130     CH.sub.3   OCH.sub.3 SO.sub.2 (tC.sub.4 H.sub.9)                   10.131     CH.sub.3   OCH.sub.3 SO.sub.2 Ph                                   10.132     CH.sub.3   OCH.sub.3 NH.sub.2                                      10.133     CH.sub.3   OCH.sub.3 NHCH.sub.3                                    10.134     CH.sub.3   OCH.sub.3 NCH.sub.3 Ph                                  10.135     CH.sub.3   OCH.sub.3 N(CH.sub.3).sub.2                             10.136     CH.sub.3   OCH.sub.3 NPh.sub.2                                     10.137     CH.sub.3   OCH.sub.3 CN                                            10.138     CH.sub.3   OCH.sub.3 NO.sub.2                                      10.139     CF.sub.3   OCH.sub.3 F                                             10.140     CF.sub.3   OCH.sub.3 Cl                                            10.141     CF.sub.3   OCH.sub.3 Br                                            10.142     CF.sub.3   OCH.sub.3 CH.sub.3                                      10.143     CF.sub.3   OCH.sub.3 C.sub.2 H.sub.5                               10.144     CF.sub.3   OCH.sub.3 nC.sub.3 H.sub.7                              10.145     CF.sub.3   OCH.sub.3 iC.sub.3 H.sub.7                              10.146     CF.sub.3   OCH.sub.3 nC.sub.4 H.sub.9                              10.147     CF.sub.3   OCH.sub.3 tC.sub.4 H.sub.9                              10.148     CF.sub.3   OCH.sub.3 Ph                                            10.149     CF.sub.3   OCH.sub.3 OH                                            10.150     CF.sub.3   OCH.sub.3 OCH.sub.3                                     10.151     CF.sub.3   OCH.sub.3 OC.sub.2 H.sub.5                              10.152     CF.sub.3   OCH.sub.3 O(nC.sub.3 H.sub.7)                           10.153     CF.sub.3   OCH.sub.3 O(iC.sub.3 H.sub.7)                           10.154     CF.sub.3   OCH.sub.3 O(nC.sub.4 H.sub.9)                           10.155     CF.sub.3   OCH.sub.3 O(tC.sub.4 H.sub.9)                           10.156     CF.sub.3   OCH.sub.3 OPh                                           10.157     CF.sub.3   OCH.sub.3 SH                                            10.158     CF.sub.3   OCH.sub.3 SCH.sub.3                                     10.159     CF.sub.3   OCH.sub.3 SC.sub.2 H.sub.5                              10.160     CF.sub.3   OCH.sub.3 S(nC.sub.3 H.sub.7)                           10.161     CF.sub.3   OCH.sub.3 S(iC.sub.3 H.sub.7)                           10.162     CF.sub.3   OCH.sub.3 S(nC.sub.4 H.sub.9)                           10.163     CF.sub.3   OCH.sub.3 S(tC.sub.4 H.sub.9)                           10.164     CF.sub.3   OCH.sub.3 SPh                                           10.165     CF.sub.3   OCH.sub.3 CCl.sub.3                                     10.166     CF.sub.3   OCH.sub.3 CH.sub.2 F                                    10.167     CF.sub.3   OCH.sub.3 CHF.sub.2                                     10.168     CF.sub.3   OCH.sub.3 CF.sub.3                                      10.169     CF.sub.3   OCH.sub.3 CF.sub.2 CHF.sub.2                            10.170     CF.sub.3   OCH.sub.3 SO.sub.3 H                                    10.171     CF.sub.3   OCH.sub.3 SO.sub.2 CH.sub.3                             10.172     CF.sub.3   OCH.sub.3 SO.sub.2 C.sub.2 H.sub.5                      10.173     CF.sub.3   OCH.sub.3 SO.sub.2 (nC.sub.3 H.sub.7)                   10.174     CF.sub.3   OCH.sub.3 SO.sub.2 (iC.sub.3 H.sub.7)                   10.175     CF.sub.3   OCH.sub.3 SO.sub.2 (nC.sub.4 H.sub.9)                   10.176     CF.sub.3   OCH.sub.3 SO.sub.2 (tC.sub.4 H.sub.9)                   10.177     CF.sub.3   OCH.sub.3 SO.sub.2 Ph                                   10.178     CF.sub.3   OCH.sub.3 NH.sub.2                                      10.179     CF.sub.3   OCH.sub.3 NHCH.sub.3                                    10.180     CF.sub.3   OCH.sub.3 NCH.sub.3 Ph                                  10.181     CF.sub.3   OCH.sub.3 N(CH.sub.3).sub.2                             10.182     CF.sub.3   OCH.sub.3 NPh.sub.2                                     10.183     CF.sub.3   OCH.sub.3 CN                                            10.184     CF.sub.3   OCH.sub.3 NO.sub.2                                      10.185     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 F                                             10.186     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 Cl                                            10.187     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 Br                                            10.188     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 CH.sub.3                                      10.189     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 C.sub.2 H.sub.5                               10.190     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 nC.sub.3 H.sub.7                              10.191     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 iC.sub.3 H.sub.7                              10.192     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 nC.sub.4 H.sub.9                              10.193     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 tC.sub.4 H.sub.9                              10.194     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 Ph                                            10.195     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 OH                                            10.196     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 OCH.sub.3                                     10.197     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 OC.sub.2 H.sub.5                              10.198     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 O(nC.sub.3 H.sub.7)                           10.199     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 O(iC.sub.3 H.sub.7)                           10.200     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 O(nC.sub.4 H.sub.9)                           10.201     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 O(tC.sub.4 H.sub.9)                           10.202     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 OPh                                           10.203     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 SH                                            10.204     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 SCH.sub.3                                     10.205     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 SC.sub.2 H.sub.5                              10.206     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 S(nC.sub.3 H.sub.7)                           10.207     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 S(iC.sub.3 H.sub.7)                           10.208     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 S(nC.sub.4 H.sub.9)                           10.209     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 S(tC.sub.4 H.sub.9)                           10.210     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 SPh                                           10.211     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 CCl.sub.3                                     10.212     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 CH.sub.2 F                                    10.213     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 CHF.sub.2                                     10.214     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 CF.sub.3                                      10.215     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 CF.sub.2 CHF.sub.2                            10.216     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 SO.sub.3 H                                    10.217     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 SO.sub.2 CH.sub.3                             10.218     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 SO.sub.2 C.sub.2 H.sub.5                      10.219     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 SO.sub.2 (nC.sub.3 H.sub.7)                   10.220     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 SO.sub.2 (iC.sub.3 H.sub.7)                   10.221     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 SO.sub.2 (nC.sub.4 H.sub.9)                   10.222     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 SO.sub.2 (tC.sub.4 H.sub.9)                   10.223     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 SO.sub.2 Ph                                   10.224     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 NH.sub.2                                      10.225     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 NHCH.sub.3                                    10.226     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 NCH.sub.3 Ph                                  10.227     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 N(CH.sub.3).sub.2                             10.228     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 NPh.sub.2                                     10.229     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 CN                                            10.230     SO.sub.2 CH.sub.3                                                                        OCH.sub.3 NO.sub.2                                      10.231     CN         OCH.sub.3 F                                             10.232     CN         OCH.sub.3 Cl                                            10.233     CN         OCH.sub.3 Br                                            10.234     CN         OCH.sub.3 CH.sub.3                                      10.235     CN         OCH.sub.3 C.sub.2 H.sub.5                               10.236     CN         OCH.sub.3 nC.sub.3 H.sub.7                              10.237     CN         OCH.sub.3 iC.sub.3 H.sub.7                              10.238     CN         OCH.sub.3 nC.sub.4 H.sub.9                              10.239     CN         OCH.sub.3 tC.sub.4 H.sub.9                              10.240     CN         OCH.sub.3 Ph                                            10.241     CN         OCH.sub.3 OH                                            10.242     CN         OCH.sub.3 OCH.sub.3                                     10.243     CN         OCH.sub.3 OC.sub.2 H.sub.5                              10.244     CN         OCH.sub.3 O(nC.sub.3 H.sub.7)                           10.245     CN         OCH.sub.3 O(iC.sub.3 H.sub.7)                           10.246     CN         OCH.sub.3 O(nC.sub.4 H.sub.9)                           10.247     CN         OCH.sub.3 O(tC.sub.4 H.sub.9)                           10.248     CN         OCH.sub.3 OPh                                           10.249     CN         OCH.sub.3 SH                                            10.250     CN         OCH.sub.3 SCH.sub.3                                     10.251     CN         OCH.sub.3 SC.sub.2 H.sub.5                              10.252     CN         OCH.sub.3 S(nC.sub.3 H.sub.7)                           10.253     CN         OCH.sub.3 S(iC.sub.3 H.sub.7)                           10.254     CN         OCH.sub.3 S(nC.sub.4 H.sub.9)                           10.255     CN         OCH.sub.3 S(tC.sub.4 H.sub.9)                           10.256     CN         OCH.sub.3 SPh                                           10.257     CN         OCH.sub.3 CCl.sub.3                                     10.258     CN         OCH.sub.3 CH.sub.2 F                                    10.259     CN         OCH.sub.3 CHF.sub.2                                     10.260     CN         OCH.sub.3 CF.sub.3                                      10.261     CN         OCH.sub.3 CF.sub.2 CHF.sub.2                            10.262     CN         OCH.sub.3 SO.sub.3 H                                    10.263     CN         OCH.sub.3 SO.sub.2 CH.sub.3                             10.264     CN         OCH.sub.3 SO.sub.2 C.sub.2 H.sub.5                      10.265     CN         OCH.sub.3 SO.sub.2 (nC.sub.3 H.sub.7)                   10.266     CN         OCH.sub.3 SO.sub.2 (iC.sub.3 H.sub.7)                   10.267     CN         OCH.sub.3 SO.sub.2 (nC.sub.4 H.sub.9)                   10.268     CN         OCH.sub.3 SO.sub.2 (tC.sub.4 H.sub.9)                   10.269     CN         OCH.sub.3 SO.sub.2 Ph                                   10.270     CN         OCH.sub.3 NH.sub.2                                      10.271     CN         OCH.sub.3 NHCH.sub.3                                    10.272     CN         OCH.sub.3 NCH.sub.3 Ph                                  10.273     CN         OCH.sub.3 N(CH.sub.3).sub.2                             10.274     CN         OCH.sub.3 NPh.sub.2                                     10.275     CN         OCH.sub.3 CN                                            10.276     CN         OCH.sub.3 NO.sub.2                                      ______________________________________                                    

SYNTHESIS EXAMPLES Example 1

Synthesis of4-(2'-sulfonylmethyl-41-trifluoromethylbenzoyl)-5-cyclopropylisothiazole7.214

The following operations are carried out with the exclusion of moisture.To 60 ml of a 1.4 M solution of (0.08 mol) of methylmagnesium bromide intoluene/tetrahydrofuran 3:1 (v/v) there are added 9.0 g (0.04 mol) of4-iodo-5-cyclopropylisothiazole in 200 ml of tetrahydrofuran withice-cooling in such a way that the reaction temperature does not exceed5° C. The reaction mixture is treated with a solution of 20.4 g (0.08mol) of 2-sulfonylmethyl-4-trifluoromethylbenzoyl chloride in 300 ml oftetrahydrofuran. After the exothermic reaction has subsided, residues oforganometallic compounds are hydrolyzed with 100 ml of 10% strengthhydrochloric acid. The reaction mixture is taken up in diethyl ether,worked up with water, dried with sodium sulfate, filtered and freed fromsolvent in vacuo. The crude product is purified on 250 g of silica gelusing cyclohexane/ethyl acetate mixtures 10:1 to 4:1 (v/v). Yield 7.2 g(43%) of colorless amorphous solid, 270 MHz ¹ H NMR (CDCl₃), δ [ppm]:1.0 (m, 2H), 1.3 (m, 2H), 2.8 (m, 1H), 3.4 (s, 3H), 7.2 (d, 1H), 8.0 (d,1H), 8.3 (s, 1H), 8.4 (s, 1H).

Other active ingredients of the general formula 1 have been obtainedanalogously by reacting the haloisothiazole compounds of the generalformula 3 with carboxylic acid derivatives of the general formula 4using the protocol described in Example 1. The resulting activeingredients of the general formula 1 are compiled in Table 5.

                                      TABLE 5                                     __________________________________________________________________________     ##STR22##                                                                    No. R.sup.2                                                                             R.sup.4                                                                            R.sup.5                                                                           R.sup.6                                                                            270 MHz .sup.1 H NMR(CDCl.sub.3),                     __________________________________________________________________________                            δ[ppm]                                          7.80                                                                              cyclopropyl                                                                         Cl   H   SO.sub.2 CH.sub.3                                                                  1.0(m, 2H), 1.4(m, 2H), 2.9(m, 1H), 3.2(s, 3H),                               7.7(d, 1H), 8.0(d, 1H), 8.1(s, 1H), 8.3(s, 1H)        11  cyclopropyl                                                                         Cl   OC.sub.2 H.sub.5                                                                  SO.sub.2 C.sub.2 H.sub.5                                                           0.9(m, 2H), 1.3(t, 3H), 1.4(m, 2H), 1.6(t, 3H),                               3.0                                                                           (m, 1H), 3.5(q, 2H), 4.4(q, 2H), 7.3(d, 1H), 8.0                              (d,                                                                           1H), 8.3(s, 1H)                                       12  CH.sub.3                                                                            Cl   H   SO.sub.2 CH.sub.3                                                                  2.9(s, 3H), 3.2(s, 3H), 7.6(d, 1H), 8.0(d, 1H),                               8.1                                                                           (s, 1H), 8.3(s, 1H)                                   13  CH.sub.3                                                                            F    H   F    2.8(s, 3H), 7.0(m, 2H), 7.7(q, 1H), 8.5(s, 1H)        14  CH.sub.3                                                                            F    H   CF.sub.3                                                                           2.9(s, 3H), 7.5(d, 1H), 7.6(d, 1H), 7.7(t, 1H),                               8.5                                                                           (s, 1H)                                               15  CH.sub.3                                                                            H    CF.sub.3                                                                          H    2.8(s, 3H), 7.7(t, 1H), 7.9(d, 1H), 8.0(d, 1H),                               8.1                                                                           (s, 1H), 8.6(s, 1H)                                   16  iC.sub.3 H.sub.7                                                                    Cl   H   SO.sub.2 CH.sub.3                                                                  1.5(d, 6H), 3.2(s, 3H), 4.1 (m, 1H), 7.6(d, 1H),                              8.0                                                                           (d, 1H), 8.1(s, 1H), 8.3(s, 1H)                       9.80                                                                              tC.sub.4 H.sub.9                                                                    Cl   H   SO.sub.2 CH.sub.3                                                                  1.7(s, 9H), 3.2(s, 3H), 7.7(d, 1H), 8.0(d, 1H),                               8.1                                                                           (s, 1H), 8.3(s, 1H)                                   9.214                                                                             tC.sub.4 H.sub.9                                                                    SO.sub.2 CH.sub.3                                                                  H   CF.sub.3                                                                           1.6(s, 9H), 3.4(s, 3H), 7.6(d, 1H), 8.0(d, 1H),                               8.2                                                                           (s, 1H), 8.5(s, 1H)                                   17  phenyl                                                                              Cl   OC.sub.2 H.sub.5                                                                  SO.sub.2 C.sub.2 H.sub.5                                                           1.2(t, 3H), 1.5(t, 3H), 3.5(q, 2H), 4.1(q, 2H),                               7.2                                                                           (d, 1H), 7.3(m, 5H), 7.8(d, 1H), 8.9(s,               __________________________________________________________________________                            1H)                                               

                                      TABLE 6                                     __________________________________________________________________________    No.                                                                              Formula             Physical Data                                          __________________________________________________________________________    6.1                                                                               ##STR23##          IR-Wave numbers in cm.sup.-1 :  1660, 1511, 1325,                             1251, 1202, 1169, 1129,  1072, 796, 699                                       1H-NMR(270 MHz; CDCl.sub.3 ; in ppm):  0.9(d2H);                              1.3(d, 2H); 2.7(m, 1H);  7.65(t, 1H); 7.85(d, 1H);                            8.0(d1H);  8.1(s, 1H); 8.45(s, 1H)                     6.2                                                                               ##STR24##          IR-Wave numbers in cm.sup.-1 :  1664, 1585, 1506,                             1429, 1375, 1338,  1264, 1245, 857, 800                                       1H-NMR(270 MHz; CDCl.sub.3 ; in ppm):  0.9(m, 2H);                            1.3(m, 2H); 2.85(m, 1H);  7.35(s, 2H); 7.45(s,                                1H); 8.3(s1, H)                                        6.3                                                                               ##STR25##          IR-Wave numbers in cm.sup.-1 :  1659, 1612, 1499,                             1428, 1339, 1270, 1143,  1103, 973, 847                                       1H-NMR(270 MHz; CDCl.sub.3 ; in ppm):  0.9(m, 2H);                            1.3(d, 2H); 2.8(m, 1H);  7.0(m, 2H); 7.65(d, 1H);                             8.4(s1, H)                                             6.4                                                                               ##STR26##          IR-Wave numbers in cm.sup.-1 :  1662, 1508, 1425,                             1330, 1215, 1176, 1135,  1077, 913, 835                                       1H-NMR(270 MHz; CDCl.sub.3 ; in ppm):  0.9(m, 2H);                            1.4(m, 2H); 2.9(m, 1H);  7.45(d, 1H); 7.55(d, 1H);                            7.7(t, 1H)8.4  (s, 1H)                                 6.5                                                                               ##STR27##          IR-Wave numbers in cm.sup.-1 :  1664, 1525, 1507,                             1350, 1340, 1263, 1246,  893, 835, 737  1H-NMR(270                            MHz; CDCl.sub.3 ; in ppm):  0.9(m, 2H); 1.3(m,                                2H); 2.9(m, 2H);  7.6(d, 1H); 8.2(m, 2H); 8.35(s,                             1H)                                                    6.6                                                                               ##STR28##          IR-Wave numbers in cm.sup.-1 :  1666, 1528, 1508,                             1430, 1383, 1340, 1279,  1262, 853, 816                                       1H-NMR(270 MHz; CDCl.sub.3 ; in ppm):  0.9(m, 2H);                            1.3(m, 2H); 2.6(s, 3H); 2.9(m,  1H); 7.4(d, 1H);                              7.8(d, 1H); 8.25(s, 1H)                                6.7                                                                               ##STR29##          1H-NMR(270 MHz; CDCl.sub.3 ; in ppm):  0.9(m, 2H);                            1.3(m, 2H); 2.8(m, 1H); 7.15  (m, 1H); 7.65(d,                                1H); 7.75(d, 1H)  8.65(s, 1H)                          6.8                                                                               ##STR30##          1H-NMR(270 MHz; CDCl.sub.3 ; in ppm):  0.9(m, 2H);                            1.3(m, 2H); 2.8(m, 1H); 3.35  (m, 3H); 7.65(d,                                1H); 8.3(s, 1H), 8.55(d,  1H); 9(d1H)                  6.9                                                                               ##STR31##          IR-Wave numbers in cm.sup.-1 :  1659, 1505, 1458,                             1427, 1335, 1260, 1246,  763, 749  1H-NMR(270 MHz;                            CDCl.sub.3 ; in ppm):  0.9(m, 2H); 1.3(m, 2H);                                2.25(s, 3H);  2.35(s, 3H); 2.85(m, 3H); 7.15(m,                               2H);  7.3(m, 3H); 8.3(s, 1H)                           6.10                                                                              ##STR32##          IR-Wave numbers in cm.sup.-1 :  1661, 1505, 1450,                             1395, 1309, 1256, 1192,  1130, 965, 811                                       1H-NMR(270 MHz; CDCl.sub.3 ; in ppm):  0.9(m, 2H);                            1.3(m, 2H); 2.35(s, 3H);  2.9(m, 1H); 3.25(s, 3H);                            4.0(s, 3H)7.25  (d, 1H); 7.9(d, 1H)8.2(s, 1H)          6.11                                                                              ##STR33##          IR-Wave numbers in cm.sup.-1 :  1649, 1602, 1586,                             1502, 1489, 1280, 1245,  1164, 873  1H-NMR(270                                MHz; CDCl.sub.3 ; in ppm):  0.9(m, 2H); 1.3(m,                                2H); 2.7(m, 1H);  7.15(m, 5H); 7.35(m, 2H); 7.8(d,                            1H); 8.0  (d, 1H); 8.5(s, 1H)                          6.12                                                                              ##STR34##          IR-Wave numbers in cm.sup.-1 :  1666, 1578, 1508,                             1429, 1382, 1338, 1272,  1084, 988, 812                                       1H-NMR(270 MHz; CDCl.sub.3 ; in ppm):  0.9(m, 2H);                            1.3(m, 2H); 2.5(s, 3H);  2.85(m, 1H); 7.15(d, 1H);                            7.4(d, 1H), 8.3  (s1H);                                6.13                                                                              ##STR35##          IR-Wave numbers in cm.sup.-1 :  1662, 1590, 1527,                             1506, 1453, 1429, 1356,  1339, 1258, 818                                      1H-NMR(270 MHz; CDCl.sub.3 ; in ppm):  0.9(m, 2H);                            1.4(m, 2H); 2.35(s, 3H);  2.85(m, 1H); 3.95(s,                                3H); 7.2(d, 1H); 7.7  (d, 1H); 8.3(s, 1H);             6.14                                                                              ##STR36##          IR-Wave numbers in cm.sup.-1 :  1666, 1506, 1430,                             1359, 1322, 1259, 1162,  1138, 804, 736                                       1H-NMR(270 MHz; CDCl.sub.3 ; in ppm):  0.9(m, 2H);                            1.25(m, 2H); 2.6(m, 1H);  3.9(s, 3H); 7.0(d, 2H);                             7.85(d, 2H);  8.45(s, 1H)                              __________________________________________________________________________

The compounds I and their salts which can be used in agriculture aresuitable as herbicides, both as isomer mixtures and in the form of thepure isomers. The herbicidal compositions comprising I are highlycapable of controlling vegetation on non-crop areas, especially at highrates of application. In crops such as wheat, rice, maize, soybeans andcotton, they act against broad-leaved weeds and grass weeds withoutdamaging the crop plants to a considerable extent. This effect isobserved mainly at low rates of application.

Depending on the application method in question, the compounds I orcompositions comprising them can additionally be used in a large numberof other crop plants for eliminating undesirable plants. Suitable cropsare, for example, the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Beta vulgaris ssp. altissima, Beta vulagris spp. rapa, Brassica napusvar. napus, Brassica napus var. napobrassica, Brassica rapa var.silvestris, Camellia sinensis, Carthamus tinctorius, Caryaillinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffeacanephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucuscarota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypiumhirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypiumvitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare,Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linumusitatissimum, Lycopersicon lycopersicum, Malus spp., Manihot esculenta,Medicago sativa, Musa spp., Nicotiana tabacum (N.rustica), Oleaeuropaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Piceaabies, Pinus spp., Pisum sativum, Prunus avium, Prunus persica, Pyruscommunis, Ribes sylestre, Ricinus communis, Saccharum officinarum,Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare),Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum,Vicia faba, Vitis vinifera, Zea mays.

In addition, the compounds I can also be used in crops which toleratethe action of herbicides as a result of breeding, including geneticengineering methods.

Application of the herbicidal compositions, or of the activeingredients, can be effected pre- or post-emergence. If the activeingredients are less well compatible with certain crop plants,application techniques may be used in which the herbicidal compositionsare sprayed, with the aid of the spraying equipment, in such a way thatthey come into as little contact as possible with the leaves of thesensitive crop plants while the active compounds reach the leaves ofundesirable plants growing underneath, or the bare soil surface(post-directed, lay-by).

The compounds I, or the herbicidal compositions comprising them, can beapplied for example in the form of directly sprayable aqueous solutions,powders, suspensions, also highly concentrated aqueous, oily or othersuspensions or dispersions, emulsions, oil dispersions, pastes, dusts,materials for spreading, or granules, by means of spraying, atomizing,dusting, spreading or pouring. The use forms depend on the intendedpurposes; in any case, they should guarantee the finest possibledistribution of the active ingredients according to the invention.

Suitable inert additives are essentially: mineral oil fractions ofmedium to high boiling point such as kerosene or diesel oil, furthermorecoal tar oils and oils of vegetable or animal origin, aliphatic, cyclicand aromatic hydrocarbons, eg. paraffin, tetrahydronaphthalene,alkylated naphthalenes or their derivatives, alkylated benzenes or theirderivatives, alcohols such as methanol, ethanol, propanol, butanol,cyclohexanol, ketones such as cyclohexanone, or strongly polar solvents,eg. amines such as N-methylpyrrolidone or water.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. To prepare emulsions, pastes or oil dispersions, thesubstances, as such or dissolved in an oil or solvent, can behomogenized in water by means of a wetting agent, tackifier, dispersantor emulsifier. Alternatively, it is possible to prepare concentratescomprising active substance, wetting agent, tackifier, dispersant oremulsifier and, if desired, solvent or oil, which are suitable fordilution with water.

Suitable surfactants (adjuvants) are the alkali metal salts, alkalineearth metal salts and ammonium salts of aromatic sulfonic acids, eg.ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, andof fatty acids, of alkyl- and alkylarylsulfonates, of alkyl lauryl ethersulfates and of fatty alcohol sulfates, salts of sulfated hexa-, hepta-and octadecanols and of fatty alcohol glycol ethers, condensates ofsulfonated naphthalene and its derivatives with formaldehyde,condensates of naphthalene or of the naphthalenesulfonic acids withphenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylatedisooctyl-, octyl- or nonylphenol, alkylphenyl polyglycol ethers,tributylphenyl polyglycol ether, alkylaryl polyether alcohols,isotridecyl alcohol, fatty alcohol/ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylenealkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters,lignin-sulfite waste liquors or methylcellulose.

Powders, materials for spreading and dusts can be prepared by mixing orgrinding the active substances together with a solid carrier.

Granules, eg. coated granules, impregnated granules and homogeneousgranules, can be prepared by binding the active ingredients to solidcarriers. Solid carriers are mineral earths such as silicas, silicagels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess,clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate,magnesium oxide, ground synthetic materials, fertilizers such asammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, andproducts of vegetable origin such as cereal meal, tree bark meal, woodmeal and nutshell meal, cellulose powders or other solid carriers.

The concentrations of the active ingredients I in the ready-to-usepreparations can be varied within wide limits. In general, theformulations comprise from 0.001 to 98% by weight, preferably 0.01 to95% by weight, of active ingredient. The active ingredients are employedin a purity of from 90% to 100%, preferably 95% to 100% (according toNMR spectrum).

For example, Compound 11 according to the invention can be formulated asfollows:

I. 20 parts by weight of Compound No. 11 are dissolved in a mixturecomposed of 80 parts by weight of alkylated benzene, 10 parts by weightof the adduct of 8 to 10 mol of ethylene oxide and 1 mol of oleic acidN-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonateand 5 parts by weight of the adduct of 40 mol of ethylene oxide and 1mol of castor oil. Pouring the solution into 100,000 parts by weight ofwater and finely distributing it therein gives an aqueous dispersioncomprising 0.02% by weight of the active ingredient.

II. 20 parts by weight of Compound 11 are dissolved in a mixturecomposed of 40 parts by weight of cyclohexanone, 30 parts by weight ofisobutanol, 20 parts by weight of the adduct of 40 mol of isooctylphenoland 10 parts by weight of the adduct of 40 mol of ethylene oxide and 1mol of castor oil. Pouring the solution into 100,000 parts by weight ofwater and finely distributing it therein gives an aqueous dispersioncomprising 0.02% by weight of the active ingredient.

III. 20 parts by weight of Active Ingredient 11 are dissolved in amixture composed of 25 parts by weight of cyclohexanone, 65 parts byweight of a mineral oil fraction of boiling point 210 to 280° C. and 10parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol ofcastor oil. Pouring the solution into 100,000 parts by weight of waterand finely distributing it therein gives an aqueous dispersioncomprising 0.02% by weight of the active ingredient.

IV. 20 parts by weight of Active Ingredient 11 are mixed thoroughly with3 parts by weight of sodium diisobutylnaphthalenesulfonate, 17 parts byweight of the sodium salt of a lignosulfonic acid from a sulfite wasteliquor and 60 parts by weight of pulverulent silica gel, and the mixtureis ground in a hammer mill. Finely distributing the mixture in 20,000parts by weight of water gives a spray mixture which comprises 0.1% byweight of the active ingredient.

V. 3 parts by weight of Active Ingredient 11 are mixed with 97 parts byweight of finely divided kaolin. This gives a dust which comprises 3% byweight of the active ingredient.

VI. 20 parts by weight of Active Ingredient 11 are mixed intimately with2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weightof fatty alcohol polyglycol ether, 2 parts by weight of the sodium saltof a phenol/urea/formaldehyde condensate and 68 parts by weight of aparaffinic mineral oil. This gives a stable oily dispersion.

VII. 1 part by weight of Compound 11 is dissolved in a mixturecomprising 70 parts by weight of cyclohexanone, 20 parts by weight ofethoxylated isooctylphenol and 10 parts by weight of ethoxylated castoroil. This gives a stable emulsion concentrate.

VIII. 1 part by weight of Compound 11 is dissolved in a mixture composedof 80 parts by weight of cyclohexanone and 20 parts by weight ofEmulphor EL (ethoxylated castor oil). This gives a stable emulsionconcentrate.

To widen the spectrum of action and to achieve synergistic effects, thebenzoylisothiazoles I can be mixed with a large number ofrepresentatives of other groups of herbicidally or growth-regulatoryactive ingredients and applied concomitantly. Components in mixturesare, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides,aminophosphoric acid and its derivatives, aminotriazoles, anilides,(het)aryloxyalkanoic acids and their derivatives, benzoic acid and itsderivatives, benzothiadiazinones, 2-aroyl-1,3-cyclohexanediones, hetarylaryl ketones, benzylisoxazolidinones, meta-CF₃ -phenyl derivatives,carbamates, quinolinecarboxylic acid and its derivatives,chloroacetanilides, cyclohexane-1,3-dione derivatives, diazines,dichloropropionic acid and its derivatives, dihydrobenzofurans,dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ether,dipyridyls, halocarboxylic acids and their derivatives, ureas,3-phenyluracils, imidazoles, imidazolinones,N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols,aryloxy- or hetaryloxyphenoxypropionic esters, phenylacetic acid and itsderivatives, phenylpropionic acid and its derivatives, pyrazoles,phenylpyrazoles, pyridazines, pyridinecarboxylic acid and itsderivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines,triazinones, triazolinones, triazolecarboxamides, uracils.

It may furthermore be advantageous to apply the compounds I, alone or incombination with other herbicides, as a mixture with further cropprotection agents, for example with pesticides or agents for controllingphytopathogenic fungi or bacteria. Also of interest is the miscibilitywith mineral salt solutions which are employed for treating nutritionaland trace element deficiencies. Non-phytotoxic oils and oil concentratesmay also be added.

The rates of application of active ingredient are from 0.001 to 3.0,preferably 0.01 to 1.0, kg/ha of active substance (a. S.) depending onthe control target, the season, target plants and the growth stage.

USE EXAMPLES

The herbicidal activity of the benzoylisothiazoles of the formula I wasdemonstrated by greenhouse experiments:

The culture containers used were plastic flowerpots containing loamysand with approximately 3.0% of humus as substrate. The seeds of thetest plants were sown separately for each species.

In the pre-emergence treatment, the active ingredients, which weresuspended or emulsified in water, were applied directly after sowing bymeans of finely distributing nozzles. The containers were irrigatedslightly to promote germination and growth and subsequently covered withtranslucent plastic shrouds until the plants had rooted. This covercaused uniform germination of the test plants unless this was adverselyaffected by the active ingredients.

To carry out the post-emergence treatment, the test plants were firstgrown to a plant height of 3 to 15 cm, depending on the plant habit, andonly then treated with the active ingredients which had been suspendedor emulsified in water. For this purpose, the test plants are eithersown directly and grown in the same containers, or they are first grownseparately as seedlings and transplanted into the test containers a fewdays prior to treatment.

The rate of application for the post-emergence treatment was 0.5, or0.25, kg/ha of a.s.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C.The test period extended over 2 to 4 weeks. During this time, the plantswere tended, and their response to the individual treatments wasevaluated.

Evaluation was carried out using a scale of from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least the aerialparts, and 0 means no damage, or normal course of growth.

The plants used in the greenhouse experiments belonged to the followingspecies:

    ______________________________________                                        Scientific Name   Common Name                                                 ______________________________________                                        Triticum aestivum wheat                                                       Abutilon theophrasti                                                                               velvetleaf                                               Chenopodium album       lamsbquarters (goosefoot)                             Solanum nigrum             black nightshade                                   ______________________________________                                    

                  TABLE 6                                                         ______________________________________                                        Selective herbicidal activity when applied                                    post-emergence in the greenhouse                                                                             11                                              ##STR37##                                                                                 Rate of application                                                           (kg/ha of a.s.)                                                               0.5    0.25                                                      Test plants    Damage in %                                                    ______________________________________                                        TRZAW          0        0                                                     ABUTH          80       80                                                    CHEAL          90       90                                                    SOLNI          90       80                                                    ______________________________________                                    

We claim:
 1. A 4-benzoylisothiazole of the formula 1 ##STR38## where thesubstituents have the following meanings: X is oxygen or sulfur;R¹ ishydrogen, alkyl, alkenyl, alkynyl; unsubstituted or substitutedalkoxycarbonyl;unsubstituted or substituted aryl, unsubstituted orsubstituted heterocyclyl or unsubstituted or substituted hetaryl; R² ishydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, it beingpossible for these radicals to have attached to them one or more of thefollowing groups: halogen, alkyl, alkenyl or alkynyl;aryl, it beingpossible for this radical to have attached to it one or more of thefollowing groups: alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy,alkynyloxy, alkylthio or alkenylthio, it being possible for theseradicals to be partially or fully halogenated or to have attached tothem one or more of the following groups: alkoxy, alkenyloxy, aryloxy,alkylsulfonyl, alkenylsulfonyl or arylsulfonyl; alkylsulfonyl oralkoxycarbonyl; unsubstituted or substituted aryloxy or unsubstituted orsubstituted arylthio; unsubstituted or substituted mono- ordialkylamino, unsubstituted or substituted mono- or diarylamino orunsubstituted or substituted N-alkyl-N-arylamino, it being possible foralkyl and aryl to be identical or different; halogen, cyano or nitro;hetaryl or heterocyclyl, it being possible for these radicals to bepartially or fully halogenated or to have attached to them one or moreof the following groups: alkyl, alkoxy or aryl, it being possible in thecase of heterocyclyl for a nitrogen ring member to have attached to itone of the following groups: alkyl, alkenyl, alkynyl, cycloalkyl,haloalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, haloalkoxy,unsubstituted or substituted aryl or unsubstituted or substitutedaryloxy; R³ is a radical of the formula 2 ##STR39## where thesubstituents have the following meanings: R⁴ -R⁸ are identical ordifferent and independently of one another are hydrogen, alkyl, alkenyl,alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl,cycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, hydroxyl,alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkylalkoxy,cycloalkylalkenyloxy, cycloalkylalkynyloxy, cycloalkenyloxy, aryloxy,arylalkoxy, arylalkenyloxy, arylalkynyloxy, thio, alkylthio,alkenylthio, alkynylthio, cycloalkylthio, cycloalkylalkylthio,cycloalkylalkenylthio, cycloalkylalkynylthio, cycloalkenylthio,arylthio, arylalkylthio, arylalkenylthio, arylalkynylthio, amino,unsubstituted or substituted mono- or dialkylamino, unsubstituted orsubstituted mono- or diarylamino, unsubstituted or substitutedN-alkyl-N-arylamino, it being possible for alkyl and aryl to beidentical or different, alkenylamino, alkynylamino, cycloalkylamino,cycloalkenylamino, sulfonyl, alkylsulfonyl, alkenylsulfonyl,alkynylsulfonyl, cycloalkylsulfonyl, cycloalkylalkylsulfonyl,cycloalkylalkenylsulfonyl, cycloalkylalkynylsulfonyl, arylsulfonyl,arylalkylsulfonyl, arylalkenylsulfonyl, arylalkynylsulfonyl, sulfoxyl,alkylsulfoxyl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl,cycloalkylalkylsulfoxyl, cycloalkylalkenylsulfoxyl,cycloalkylalkynylsulfoxyl, arylsulfoxyl, arylalkylsulfoxyl,arylalkenylsulfoxyl, arylalkynylsulfoxyl, aminosulfonyl, unsubstitutedor substituted mono- or dialkylaminosulfonyl, unsubstituted orsubstituted diarylaminosulfonyl, unsubstituted or substitutedN-alkyl-N-arylaminosulfonyl, it being possible for alkyl and aryl to beidentical or different, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl,cycloalkylcarbonyl, cycloalkylalkylcarbonyl, cycloalkylalkenylcarbonyl,cycloalkylalkynylcarbonyl, arylcarbonyl, arylalkylcarbonyl,arylalkenylcarbonyl, arylalkynylcarbonyl, carboxyl, alkoxycarbonyl,alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl,cycloalkylalkoxycarbonyl, cycloalkylalkenyloxycarbonyl,cycloalkylalkynyloxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl,arylalkenyloxycarbonyl, arylalkynyloxycarbonyl, aminocarbonyl,unsubstituted or substituted mono- or dialkylaminocarbonyl,unsubstituted or substituted mono- or diarylaminocarbonyl, unsubstitutedor substituted N-alkyl-N-arylaminocarbonyl, it being possible for alkyland aryl to be identical or different, unsubstituted or substitutedmono- or dialkylcarbonylamino, unsubstituted or substituted mono- ordiarylcarbonylamino, unsubstituted or substitutedN-alkyl-N-arylcarbonylamino, it being possible for alkyl and aryl to beidentical or different; alkoxyaminocarbonyl, alkenyloxyaminocarbonyl,alkynyloxycarbonylamino, cycloalkoxycarbonylamino,cycloalkylalkoxycarbonylamino, cycloalkylalkenyloxycarbonylamino,cycloalkylalkynyloxycarbonylamino, aryloxycarbonylamino,arylalkoxycarbonylamino, arylalkenyloxycarbonylamino,arylalkynyloxycarbonylamino, halogen, haloalkyl, haloalkenyl,haloalkynyl, haloalkoxy, haloalkenyloxy, haloalkynyloxy, haloalkylthio,haloalkenylthio, haloalkynylthio, haloalkylamino, haloalkenylamino,haloalkynylamino, haloalkylsulfonyl, haloalkenylsulfonyl,haloalkynylsulfonyl, haloalkylsulfoxyl, haloalkenylsulfoxyl,haloalkynylsulfoxyl, haloalkylcarbonyl, haloalkenylcarbonyl,haloalkynylcarbonyl, haloalkoxycarbonyl, haloalkenyloxycarbonyl,haloalkynyloxycarbonyl, haloalkylaminocarbonyl,haloalkenylaminocarbonyl, haloalkynylaminocarbonyl,haloalkoxycarbonylamino, haloalkenyloxycarbonylamino,haloalkynyloxycarbonylamino; cyano or nitro or one of the followinggroups: ##STR40## or R⁴, R⁵ together form a five- or six-membered,saturated or unsaturated, aromatic or non-aromatic, unsubstituted orsubstituted alkylene, alkenylene or alkdienylene chain; or R⁵, R⁶together form a five- or six-membered, saturated or unsaturated,aromatic or non-aromatic, unsubstituted or substituted alkylene,alkenylene or alkdienylene chain;with the exception of4-benzoyl-3-phenylisothiazole, 4-(4'-chlorobenzoyl)-3-methylisothiazole,4-benzoyl-3,5-dimethylisothiazole,4-(4'-hydroxymethylcarbonylaminobenzoyl)-isothiazole and4-(3',5'-tertiary-butyl-4'-hydroxybenzoyl)-isothiazole; or a salt of the4-benzoylisothiazole of the formula 1 which is conventionally used inagriculture.
 2. The 4-benzoylisothiazole of the formula 1 defined inclaim 1 where X is oxygen.
 3. The 4-benzoylisothiazole of the formula 1defined in claim 1 where R¹ is hydrogen or unsubstituted or substitutedalkoxycarbonyl.
 4. The 4-benzoylisothiazole of the formula 1 defined inclaim 1 where R² is alkyl, cycloalkyl, aryl which is unsubstituted ormono- or polysubstituted by halogen or haloalkyl, or hetaryl which isunsubstituted or mono- or polysubstituted by halogen.
 5. The4-benzoylisothiazole of the formula 1 defined in claim 1 where R² ismethyl, ethyl, isopropyl, tert-butyl, cyclopropyl, 1-methylcyclopropyl,3-trifluoromethylaryl, 2,4-difluoroaryl, 1,3-benzodioxolyl,2,2-difluoro-1,3-benzodioxolyl, 1,3-benzoxathiolyl,3,3-dioxo-1,3-benzoxathiolyl, benzoxazolyl, pyrazolyl or thienyl.
 6. The4-benzoylisothiazole of the formula 1 defined in claim 1 whereR⁴ -R⁸ areidentical or different and independently of one another are hydrogen,alkyl, cycloalkyl, aryl, hydroxyl, alkoxy, cycloalkoxy, aryloxy, thio,alkylthio, cycloalkylthio, arylthio, amino, in each case unsubstitutedor substituted mono- or dialkylamino or mono- or diarylamino orN-alkyl-N-arylamino, it being possible for alkyl and aryl to beidentical or different, cycloalkylamino, sulfonyl, alkylsulfonyl,cycloalkylsulfonyl, arylsulfonyl, sulfoxyl, alkylsulfoxyl,cycloalkylsulfoxyl, arylsulfoxyl, alkylcarbonyl, cycloalkylcarbonyl,arylcarbonyl, carboxyl, alkoxycarbonyl, cycloalkoxycarbonyl,aryloxycarbonyl, aminocarbonyl, in each case unsubstituted orsubstituted mono- or dialkylaminocarbonyl or mono- ordiarylaminocarbonyl or N-alkyl-N-arylaminocarbonyl, it being possiblefor alkyl and aryl to be identical or different, alkoxyaminocarbonyl,cycloalkoxycarbonylamino, aryloxycarbonylamino, halogen, haloalkyl,haloalkoxy, haloalkylthio, haloalkylamino, haloalkylsulfonyl,haloalkylsulfoxyl, haloalkylcarbonyl, haloalkoxycarbonyl,haloalkylaminocarbonyl, haloalkoxycarbonylamino; cyano or nitro; or R⁴,R⁵ together form a five- or six-membered, saturated or unsaturated,aromatic or non-aromatic, unsubstituted or substituted alkylene,alkenylene or alkdienylene chain; or R⁵, R⁶ together form a five- orsix-membered, saturated or unsaturated, aromatic or non-aromatic,unsubstituted or substituted alkylene, alkenylene or alkdienylene chain.7. The 4-benzoylisothiazole of the formula 1 defined in claim 1 where R³is a radical of the formula 2a-g ##STR41## where the substituents havethe following meanings: R⁴ -R⁸ are identical or different andindependently of one another are alkyl, alkenyl, alkynyl, cycloalkyl,cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, aryl, arylalkyl,arylalkenyl, arylalkynyl, hydroxyl, alkoxy, alkenyloxy, alkynyloxy,cycloalkoxy, cycloalkylalkoxy, cycloalkylalkenyloxy,cycloalkylalkynyloxy, aryloxy, arylalkoxy, arylalkenyloxy,arylalkynyloxy, thio, alkylthio, alkenylthio, alkynylthio,cycloalkylthio, cycloalkylalkylthio, cycloalkylalkenylthio,cycloalkylalkynylthio, arylthio, arylalkylthio, arylalkenylthio,arylalkynylthio, amino, unsubstituted or substituted mono- ordialkylamino, unsubstituted or substituted mono- or diarylamino,unsubstituted or substituted N-alkyl-N-arylamino, it being possible foralkyl and aryl to be identical or different, sulfonyl, alkylsulfonyl,cycloalkylsulfonyl, cycloalkylalkylsulfonyl, cycloalkylalkenylsulfonyl,cycloalkylalkynylsulfonyl, arylsulfonyl, arylalkylsulfonyl,arylalkenylsulfonyl, arylalkynylsulfonyl, sulfoxyl, alkylsulfoxyl,alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl,cycloalkylalkylsulfoxyl, cycloalkylalkenylsulfoxyl,cycloalkylalkynylsulfoxyl, arylsulfoxyl, arylalkylsulfoxyl,arylalkenylsulfoxyl, arylalkynylsulfoxyl, aminosulfonyl, unsubstitutedor substituted mono- or dialkylaminosulfonyl, unsubstituted orsubstituted diarylaminosulfonyl, unsubstituted or substitutedN-alkyl-N-arylaminosulfonyl, it being possible for alkyl and aryl to beidentical or different, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl,cycloalkylcarbonyl, cycloalkylalkylcarbonyl, cycloalkylalkenylcarbonyl,cycloalkylalkynylcarbonyl, arylcarbonyl, arylalkylcarbonyl,arylalkenylcarbonyl, arylalkynylcarbonyl, carboxyl, alkoxycarbonyl,alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl,cycloalkylalkoxycarbonyl, cycloalkylalkenyloxycarbonyl,cycloalkylalkynyloxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl,arylalkenyloxycarbonyl, arylalkynyloxycarbonyl, aminocarbonyl,unsubstituted or substituted mono- or dialkylaminocarbonyl,unsubstituted or substituted mono- or diarylaminocarbonyl, unsubstitutedor substituted N-alkyl-N-arylaminocarbonyl, it being possible for alkyland aryl to be identical or different, unsubstituted or substitutedmono- or dialkylcarbonylamino, unsubstituted or substituted mono- ordiarylcarbonylamino, unsubstituted or substitutedN-alkyl-N-arylcarbonylamino, it being possible for alkyl and aryl to beidentical or different; alkoxyaminocarbonyl, alkenyloxyaminocarbonyl,alkynyloxycarbonylamino, cycloalkoxycarbonylamino,cycloalkylalkoxycarbonylamino, cycloalkylalkenyloxycarbonylamino,cycloalkylalkynyloxycarbonylamino, aryloxycarbonylamino,arylalkoxycarbonylamino, arylalkenyloxycarbonylamino,arylalkynyloxycarbonylamino, halogen, haloalkyl, haloalkenyl,haloalkynyl, haloalkoxy, haloalkenyloxy, haloalkynyloxy, haloalkylthio,haloalkenylthio, haloalkynylthio, haloalkylamino, haloalkenylamino,haloalkynylamino, haloalkylsulfonyl, haloalkenylsulfonyl,haloalkynylsulfonyl, haloalkylcarbonyl, haloalkenylcarbonyl,haloalkynylcarbonyl, haloalkoxycarbonyl, haloalkenyloxycarbonyl,haloalkynyloxycarbonyl, haloalkylaminocarbonyl,haloalkenylaminocarbonyl, haloalkynylaminocarbonyl,haloalkoxycarbonylamino, haloalkenyloxycarbonylamino,haloalkynyloxycarbonylamino; cyano or nitro.
 8. The 4-benzoylisothiazoleof the formula 1 defined in claim 1 where R³ is a radical of the formula2h-l ##STR42## where the substituents have the following meanings: R⁴-R⁸ are identical or different and independently of one another are alow-molecular radical selected from the group consisting of alkyl,alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl,cycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, hydroxyl,alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkylalkoxy,cycloalkylalkenyloxy, cycloalkylalkynyloxy, aryloxy, arylalkoxy,arylalkenyloxy, arylalkynyloxy, thio, alkylthio, alkenylthio,alkynylthio, cycloalkylthio, cycloalkylalkylthio, cycloalkylalkenylthio,cycloalkylalkynylthio, arylthio, arylalkylthio, arylalkenylthio,arylalkynylthio, amino, unsubstituted or substituted mono- ordialkylamino, unsubstituted or substituted mono- or diarylamino,unsubstituted or substituted N-alkyl-N-arylamino, it being possible foralkyl and aryl to be identical or different, sulfonyl, alkylsulfonyl,cycloalkylsulfonyl, cycloalkylalkylsulfonyl, cycloalkylalkenylsulfonyl,cycloalkylalkynylsulfonyl, arylsulfonyl, arylalkylsulfonyl,arylalkenylsulfonyl, arylalkynylsulfonyl, sulfoxyl, alkylsulfoxyl,alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl,cycloalkylalkylsulfoxyl, cycloalkylalkenylsulfoxyl,cycloalkylalkynylsulfoxyl, arylsulfoxyl, arylalkylsulfoxyl,arylalkenylsulfoxyl, arylalkynylsulfoxyl, aminosulfonyl, unsubstitutedor substituted mono- or dialkylaminosulfonyl, unsubstituted orsubstituted diarylaminosulfonyl, unsubstituted or substitutedN-alkyl-N-arylaminosulfonyl, it being possible for alkyl and aryl to beidentical or different, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl,cycloalkylcarbonyl, cycloalkylalkylcarbonyl, cycloalkylalkenylcarbonyl,cycloalkylalkynylcarbonyl, arylcarbonyl, arylalkylcarbonyl,arylalkenylcarbonyl, arylalkynylcarbonyl, carboxyl, alkoxycarbonyl,alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl,cycloalkylalkoxycarbonyl, cycloalkylalkenyloxycarbonyl,cycloalkylalkynyloxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl,arylalkenyloxycarbonyl, arylalkynyloxycarbonyl, aminocarbonyl,unsubstituted or substituted mono- or dialkylaminocarbonyl,unsubstituted or substituted mono- or diarylaminocarbonyl, unsubstitutedor substituted N-alkyl-N-arylaminocarbonyl, it being possible for alkyland aryl to be identical or different, unsubstituted or substitutedmono- or dialkylcarbonylamino, unsubstituted or substituted mono- ordiarylcarbonylamino, unsubstituted or substitutedN-alkyl-N-arylcarbonylamino, it being possible for alkyl and aryl to beidentical or different, alkoxyaminocarbonyl, alkenyloxyaminocarbonyl,alkynyloxycarbonylamino, cycloalkoxycarbonylamino,cycloalkylalkoxycarbonylamino, cycloalkylalkenyloxycarbonylamino,cycloalkylalkynyloxycarbonylamino, aryloxycarbonylamino,arylalkoxycarbonylamino, arylalkenyloxycarbonylamino,arylalkynyloxycarbonylamino, halogen, haloalkyl, haloalkenyl,haloalkynyl, haloalkoxy, haloalkenyloxy, haloalkynyloxy, haloalkylthio,haloalkenylthio, haloalkynylthio, haloalkylamino, haloalkenylamino,haloalkynylamino, haloalkylsulfonyl, haloalkenylsulfonyl,haloalkynylsulfonyl, haloalkylcarbonyl, haloalkenylcarbonyl,haloalkynylcarbonyl, haloalkoxycarbonyl, haloalkenyloxycarbonyl,haloalkynyloxycarbonyl, haloalkylaminocarbonyl,haloalkenylaminocarbonyl, haloalkynylaminocarbonyl,haloalkoxycarbonylamino, haloalkenyloxycarbonylamino,haloalkynyloxycarbonylamino; cyano or nitro, orR⁴, R⁵ together form afive- or six-membered, saturated or unsaturated, aromatic ornon-aromatic, unsubstituted or substituted alkylene, alkenylene oralkdienylene chain; or R⁵, R⁶ together form a five- or six-membered,saturated or unsaturated, aromatic or non-aromatic, unsubstituted orsubstituted alkylene, alkenylene or alkdienylene chain.
 9. The4-benzoylisothiazole of the formula 1 defined in claim 1 where R³ is aradical of the formula 2b ##STR43## and R⁴ and R⁶ are identical ordifferent and independently of one another are alkyl, alkoxy, aryloxy,alkylsulfonyl, halogen or haloalkyl.
 10. The 4-benzoylisothiazole of theformula 1 defined in claim 9 whereR⁴ and R⁶ are identical or differentand independently of one another are methylsulfonyl, ethylsulfonyl,difluoromethyl, trifluoromethyl, tetrafluoroethyl or trichloromethyl.11. The 4-benzoylisothiazole of the formula 1 defined in claim 1 whereR³ is a radical of the formula 2h ##STR44## and R⁴, R⁵ and R⁶ areidentical or different and independently of one another are alkyl,alkoxy, aryloxy, alkylsulfonyl, halogen or haloalkyl.
 12. The4-benzoylisothiazole of the formula 1 defined in claim 11 whereR⁴, R⁵and R⁶ are identical or different and independently of one another are alow-molecular radical selected from the group consisting of methyl,ethyl, methoxy, ethoxy, phenoxy, methylsulfonyl, ethylsulfonyl,fluorine, bromine, iodine, difluoromethyl, trifluoromethyl,tetrafluoroethyl or trichloromethyl.
 13. The 4-benzoylisothiazole of theformula 1 defined in claim 1 where R³ is2-chloro-4-methylsulfonylphenyl.
 14. The 4-benzoylisothiazole of theformula 1 defined in claim 1 where R³ is2-methylsulfonyl-4-trifluoromethylphenyl.
 15. The 4-benzoylisothiazoleof the formula 1 defined in claim 1 where R³ is2-chloro-3-methoxy-4-methylphenyl or 2-chloro-3-ethoxy-4-ethylphenyl.16. A 4-benzoylisothiazole of the formula 1 ##STR45## where thesubstituents have the following meanings: X is oxygen or sulfur;R¹ ishydrogen, alkyl, alkenyl, alkynyl; unsubstituted or substitutedalkoxycarbonyl;unsubstituted or substituted aryl, unsubstituted orsubstituted heterocyclyl or unsubstituted or substituted hetaryl; R² ishydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, it beingpossible for these radicals to have attached to them one or more of thefollowing groups: halogen, alkyl, alkenyl or alkynyl;aryl, it beingpossible for this radical to have attached to it one or more of thefollowing groups: alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy,alkynyloxy, alkylthio or alkenylthio, it being possible for theseradicals to be partially or fully halogenated or to have attached tothem one or more of the following groups: alkoxy, alkenyloxy, aryloxy,alkylsulfonyl, alkenylsulfonyl or arylsulfonyl; alkylsulfonyl oralkoxycarbonyl; unsubstituted or substituted aryloxy or unsubstituted orsubstituted arylthio; unsubstituted or substituted mono- ordialkylamino, unsubstituted or substituted mono- or diarylamino orunsubstituted or substituted N-alkyl-N-arylamino, it being possible foralkyl and aryl to be identical or different; halogen, cyano or nitro;hetaryl or heterocyclyl, it being possible for these radicals to bepartially or fully halogenated or to have attached to them one or moreof the following groups: alkyl, alkoxy or aryl, it being possible in thecase of heterocyclyl for a nitrogen ring member to have attached to itone of the following groups: alkyl, alkenyl, alkynyl, cycloalkyl,haloalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, haloalkoxy,unsubstituted or substituted aryl or unsubstituted or substitutedaryloxy; R³ is a radical of the formula 2 ##STR46## wherein R⁴ to R⁸ areindependently of one another hydrogen, alkyl, alkenyl, alkynyl,cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl,cycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, hydroxyl,alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkylalkoxy,cycloalkylalkenyloxy, cycloalkylalkynyloxy, cycloalkenyloxy, aryloxy,arylalkoxy, arylalkenyloxy, arylalkynyloxy, thio, alkylthio,alkenylthio, alkynylthio, cycloalkylthio, cycloalkylalkylthio,cycloalkylalkenylthio, cycloalkylalkynylthio, cycloalkenylthio,arylthio, arylalkylthio, arylalkenylthio, arylalkynylthio, amino,unsubstituted or substituted mono- or dialkylamino, unsubstituted orsubstituted mono- or diarylamino, unsubstituted or substitutedN-alkyl-N-arylamino, it being possible for alkyl and aryl to beidentical or different, alkenylamino, alkynylamino, cycloalkylamino,cycloalkenylamino, sulfonyl, alkylsulfonyl, alkenylsulfonyl,alkynylsulfonyl, cycloalkylsulfonyl, cycloalkylalkylsulfonyl,cycloalkylalkenylsulfonyl, cycloalkylalkynylsulfonyl, arylsulfonyl,arylalkylsulfonyl, arylalkenylsulfonyl, arylalkynylsulfonyl, sulfoxyl,alkylsulfoxyl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl,cycloalkylalkylsulfoxyl, cycloalkylalkenylsulfoxyl,cycloalkylalkynylsulfoxyl, arylsulfoxyl, arylalkylsulfoxyl,arylalkenylsulfoxyl, arylalkynylsulfoxyl, aminosulfonyl, unsubstitutedor substituted mono- or dialkylaminosulfonyl, unsubstituted orsubstituted diarylaminosulfonyl, unsubstituted or substitutedN-alkyl-N-arylaminosulfonyl, it being possible for alkyl and aryl to beidentical or different, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl,cycloalkylcarbonyl, cycloalkylalkylcarbonyl, cycloalkylalkenylcarbonyl,cycloalkylalkynylcarbonyl, arylcarbonyl, arylalkylcarbonyl,arylalkenylcarbonyl, arylalkynylcarbonyl, carboxyl, alkoxycarbonyl,alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl,cycloalkylalkoxycarbonyl, cycloalkylalkenyloxycarbonyl,cycloalkylalkynyloxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl,arylalkenyloxycarbonyl, arylalkynyloxycarbonyl, aminocarbonyl,unsubstituted or substituted mono- or dialkylaminocarbonyl,unsubstituted or substituted mono- or diarylaminocarbonyl, unsubstitutedor substituted N-alkyl-N-arylaminocarbonyl, it being possible for alkyland aryl to be identical or different, unsubstituted or substitutedmono- or dialkylcarbonylamino, unsubstituted or substituted mono- ordiarylcarbonylamino, unsubstituted or substitutedN-alkyl-N-arylcarbonylamino, it being possible for alkyl and aryl to beidentical or different; alkoxyaminocarbonyl, alkenyloxyaminocarbonyl,alkynyloxycarbonylamino, cycloalkoxycarbonylamino,cycloalkylalkoxycarbonylamino, cycloalkylalkenyloxycarbonylamino,cycloalkylalkynyloxycarbonylamino, aryloxycarbonylamino,arylalkoxycarbonylamino, arylalkenyloxycarbonylamino,arylalkynyloxycarbonylamino, halogen, haloalkyl, haloalkenyl,haloalkynyl, haloalkoxy, haloalkenyloxy, haloalkynyloxy, haloalkylthio,haloalkenylthio, haloalkynylthio, haloalkylamino, haloalkenylamino,haloalkynylamino, haloalkylsulfonyl, haloalkenylsulfonyl,haloalkynylsulfonyl, haloalkylsulfoxyl, haloalkenylsulfoxyl,haloalkynylsulfoxyl, haloalkylcarbonyl, haloalkenylcarbonyl,haloalkynylcarbonyl, haloalkoxycarbonyl, haloalkenyloxycarbonyl,haloalkynyloxycarbonyl, haloalkylaminocarbonyl,haloalkenylaminocarbonyl, haloalkynylaminocarbonyl,haloalkoxycarbonylamino, haloalkenyloxycarbonylamino,haloalkynyloxycarbonylamino; cyano or nitro or one of the followinggroups: ##STR47## or R⁴, R⁵ together form a five- or six-membered,saturated or unsaturated, aromatic or non-aromatic, unsubstituted orsubstituted alkylene, alkenylene or alkdienylene chain; or R⁵, R⁶together form a five- or six-membered, saturated or unsaturated,aromatic or non-aromatic, unsubstituted or substituted alkylene,alkenylene or alkdienylene chain;wherein at least one of R⁴ to R⁸ isother than hydrogen, and with the exception of4-(4'-chlorobenzoyl)-3-methylisothiazole,4-(4'-hydroxymethylcarbonylaminobenzoyl)-isothiazole and4-(3',5'-tertiary-butyl-4'-hydroxybenzoyl)-isothiazole; or a salt of the4-benzoylisothiazole of the formula 1 which is conventionally used inagriculture.
 17. The 4-benzoylisothiazole of the formula 1 defined inclaim 16, wherein R⁴ to R⁸ are independently of one another hydrogen,alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl,cycloalkylalkenyl, cycloalkylalkynyl, aryl, arylalkyl, arylalkenyl,arylalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy,cycloalkylalkoxy, cycloalkylalkenyloxy, cycloalkylalkynyloxy,cycloalkenyloxy, aryloxy, arylalkoxy, arylalkenyloxy, arylalkynyloxy,thio, alkylthio, alkenylthio, alkynylthio, cycloalkylthio,cycloalkylalkylthio, cycloalkylalkenylthio, cycloalkylalkynylthio,cycloalkenylthio, arylthio, arylalkylthio, arylalkenylthio,arylalkynylthio, amino, unsubstituted or substituted mono- ordialkylamino, unsubstituted or substituted mono- or diarylamino,unsubstituted or substituted N-alkyl-N-arylamino, it being possible foralkyl and aryl to be identical or different, alkenylamino, alkynylamino,cycloalkylamino, cycloalkenylamino, sulfonyl, alkylsulfonyl,alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl,cycloalkylalkylsulfonyl, cycloalkylalkenylsulfonyl,cycloalkylalkynylsulfonyl, arylsulfonyl, arylalkylsulfonyl,arylalkenylsulfonyl, arylalkynylsulfonyl, sulfoxyl, alkylsulfoxyl,alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl,cycloalkylalkylsulfoxyl, cycloalkylalkenylsulfoxyl,cycloalkylalkynylsulfoxyl, arylsulfoxyl, arylalkylsulfoxyl,arylalkenylsulfoxyl, arylalkynylsulfoxyl, aminosulfonyl, unsubstitutedor substituted mono- or dialkylaminosulfonyl, unsubstituted orsubstituted diarylaminosulfonyl, unsubstituted or substitutedN-alkyl-N-arylaminosulfonyl, it being possible for alkyl and aryl to beidentical or different, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl,cycloalkylcarbonyl, cycloalkylalkylcarbonyl, cycloalkylalkenylcarbonyl,cycloalkylalkynylcarbonyl, arylcarbonyl, arylalkylcarbonyl,arylalkenylcarbonyl, arylalkynylcarbonyl, carboxyl, alkoxycarbonyl,alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl,cycloalkylalkoxycarbonyl, cycloalkylalkenyloxycarbonyl,cycloalkylalkynyloxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl,arylalkenyloxycarbonyl, arylalkynyloxycarbonyl, aminocarbonyl,unsubstituted or substituted mono- or dialkylaminocarbonyl,unsubstituted or substituted mono- or diarylaminocarbonyl, unsubstitutedor substituted N-alkyl-N-arylaminocarbonyl, it being possible for alkyland aryl to be identical or different, unsubstituted or substitutedmono- or dialkylcarbonylamino, unsubstituted or substituted mono- ordiarylcarbonylamino, unsubstituted or substitutedN-alkyl-N-arylcarbonylamino, it being possible for alkyl and aryl to beidentical or different; alkoxyaminocarbonyl, alkenyloxyaminocarbonyl,alkynyloxycarbonylamino, cycloalkoxycarbonylamino,cycloalkylalkoxycarbonylamino, cycloalkylalkenyloxycarbonylamino,cycloalkylalkynyloxycarbonylamino, aryloxycarbonylamino,arylalkoxycarbonylamino, arylalkenyloxycarbonylamino,arylalkynyloxycarbonylamino, halogen, haloalkyl, haloalkenyl,haloalkynyl, haloalkoxy, haloalkenyloxy, haloalkynyloxy, haloalkylthio,haloalkenylthio, haloalkynylthio, haloalkylamino, haloalkenylamino,haloalkynylamino, haloalkylsulfonyl, haloalkenylsulfonyl,haloalkynylsulfonyl, haloalkylsulfoxyl, haloalkenylsulfoxyl,haloalkynylsulfoxyl, haloalkylcarbonyl, haloalkenylcarbonyl,haloalkynylcarbonyl, haloalkoxycarbonyl, haloalkenyloxycarbonyl,haloalkynyloxycarbonyl, haloalkylaminocarbonyl,haloalkenylaminocarbonyl, haloalkynylaminocarbonyl,haloalkoxycarbonylamino, haloalkenyloxycarbonylamino,haloalkynyloxycarbonylamino; cyano or nitro or one of the followinggroups: ##STR48## or R⁴, R⁵ together form a five- or six-membered,saturated or unsaturated, aromatic or non-aromatic, unsubstituted orsubstituted alkylene, alkenylene or alkdienylene chain; orR⁵, R⁶together form a five- or six-membered, saturated or unsaturated,aromatic or non-aromatic, unsubstituted or substituted alkylene,alkenylene or alkdienylene chain;and wherein at least one of R⁴ to R⁸ isother than hydrogen.
 18. The 4-benzoylisothiazole of the formula 1defined in claim 16, wherein one, two or three of R⁴ to R⁸ are otherthan hydrogen.
 19. The 4-benzoylisothiazole of the formula 1 defined inclaim 17, wherein one, two or three of R⁴ to RB are other than hydrogen.20. A herbicidal composition comprising a 4-benzoylisothiazole of theformula 1 defined in claim 1 and inert additives.
 21. A method ofcontrolling undesirable vegetation which comprises treating theundesired plants and/or their habitat with a herbicidally active amountof a 4-benzoylisothiazole of the formula 1 defined in claim
 1. 22. Aprocess for the preparation of the 4-benzoylisothiazole of the formula 1defined in claim 1 which comprises reacting a haloisothiazole compoundof the formula 3 ##STR49## where Y is halogen with elemental magnesium,an organomagnesium or an organolithium compound and with a carboxylicacid of the formula 4 ##STR50## where R¹⁰ is halogen,N-alkoxy-N-alkylamino or cyano in a temperature range of from -78° C. to111° C. in the presence of an inert solvent.
 23. A process for thepreparation of the 4-benzoylisothiazole of the formula 1 defined inclaim 1 which comprises reacting a halobenzene of the formula 5##STR51## where Y is halogen with elemental magnesium, anorganomagnesium or an organolithium compound and with aisothiazolecarboxylic acid of the formula 6a or 6b ##STR52## where R¹⁰is halogen or N-alkoxy-N-alkylamino in a temperature range of from -78°C. to 111° C. in the presence of an inert solvent.